TY  - JOUR
AU  - Kovačević, Strahinja
AU  - Karadzić-Banjac, Milica
AU  - Podunavac-Kuzmanović, Sanja
AU  - Milošević, Nataša
AU  - Curcić, Jelena
AU  - Vulić, Jelena
AU  - Seregelj, Vanja
AU  - Banjac, Nebojša
AU  - Ušćumlić, Gordana
PY  - 2020
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5885
AB  - The present study is focused on a series of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimide derivatives, as potential anticonvulsants. The retention behavior of eleven succinimide derivatives was determined by using reversed phase high performance liquid chromatography (RP-HPLC) and reversed phase high performance thin layer chromatography (RP-HPTLC). The estimated retention behavior was correlated with partition (logP) and distribution coefficients (logD). These high correlations pointed out that the determined retention parameters (logK(0) and R-M(0)) can be considered chromatographic (anisotropic) lipophilicity of the studied succinimide derivatives. The structural properties, which dominantly affect the chromatographic lipophilicity, were determined as well. The significant correlations between the chromatographic lipophilicity and plasma protein binding (PPB), Madin-Darby Canine Kidney (MDCK) cells permeability, volume of distribution (Vd) and absorption constant (Ka) indicate the strong influence of lipophilicity on pharmacokinetics of 1-aryl-3-ethyl-3-methylsuccinimide derivatives. These derivatives have also been tested applying Comprehensive Medicinal Chemistry (CMC) drug-like rules which confirmed their drug-like properties. Besides, their blood-brain penetration (BBB) ability has been estimated applying the set of Clark's rules and by using Pre-ADMET software. Regarding toxicity, it was predicted that only one compound from the set might have toxic effects by blocking the hERG potassium channel. The present study reveals which molecular features in the structure of novel succinimide derivatives could be crucial for their lipophilicity, and consequently for their pharmacokinetic properties. The results indicate that the newly synthesized series of succinimide derivatives should be further considered in design of novel anticonvulsants.
PB  - Elsevier Sci Ltd, Oxford
T2  - Computational Biology and Chemistry
T1  - Chromatographic and computational screening of anisotropic lipophilicity and pharmacokinetics of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimides
VL  - 84
DO  - 10.1016/j.compbiolchem.2019.107161
ER  - 

@article{
author = "Kovačević, Strahinja and Karadzić-Banjac, Milica and Podunavac-Kuzmanović, Sanja and Milošević, Nataša and Curcić, Jelena and Vulić, Jelena and Seregelj, Vanja and Banjac, Nebojša and Ušćumlić, Gordana",
year = "2020",
abstract = "The present study is focused on a series of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimide derivatives, as potential anticonvulsants. The retention behavior of eleven succinimide derivatives was determined by using reversed phase high performance liquid chromatography (RP-HPLC) and reversed phase high performance thin layer chromatography (RP-HPTLC). The estimated retention behavior was correlated with partition (logP) and distribution coefficients (logD). These high correlations pointed out that the determined retention parameters (logK(0) and R-M(0)) can be considered chromatographic (anisotropic) lipophilicity of the studied succinimide derivatives. The structural properties, which dominantly affect the chromatographic lipophilicity, were determined as well. The significant correlations between the chromatographic lipophilicity and plasma protein binding (PPB), Madin-Darby Canine Kidney (MDCK) cells permeability, volume of distribution (Vd) and absorption constant (Ka) indicate the strong influence of lipophilicity on pharmacokinetics of 1-aryl-3-ethyl-3-methylsuccinimide derivatives. These derivatives have also been tested applying Comprehensive Medicinal Chemistry (CMC) drug-like rules which confirmed their drug-like properties. Besides, their blood-brain penetration (BBB) ability has been estimated applying the set of Clark's rules and by using Pre-ADMET software. Regarding toxicity, it was predicted that only one compound from the set might have toxic effects by blocking the hERG potassium channel. The present study reveals which molecular features in the structure of novel succinimide derivatives could be crucial for their lipophilicity, and consequently for their pharmacokinetic properties. The results indicate that the newly synthesized series of succinimide derivatives should be further considered in design of novel anticonvulsants.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Computational Biology and Chemistry",
title = "Chromatographic and computational screening of anisotropic lipophilicity and pharmacokinetics of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimides",
volume = "84",
doi = "10.1016/j.compbiolchem.2019.107161"
}

Kovačević, S., Karadzić-Banjac, M., Podunavac-Kuzmanović, S., Milošević, N., Curcić, J., Vulić, J., Seregelj, V., Banjac, N.,& Ušćumlić, G.. (2020). Chromatographic and computational screening of anisotropic lipophilicity and pharmacokinetics of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimides. in Computational Biology and Chemistry
Elsevier Sci Ltd, Oxford., 84.
https://doi.org/10.1016/j.compbiolchem.2019.107161

Kovačević S, Karadzić-Banjac M, Podunavac-Kuzmanović S, Milošević N, Curcić J, Vulić J, Seregelj V, Banjac N, Ušćumlić G. Chromatographic and computational screening of anisotropic lipophilicity and pharmacokinetics of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimides. in Computational Biology and Chemistry. 2020;84.
doi:10.1016/j.compbiolchem.2019.107161 .

Kovačević, Strahinja, Karadzić-Banjac, Milica, Podunavac-Kuzmanović, Sanja, Milošević, Nataša, Curcić, Jelena, Vulić, Jelena, Seregelj, Vanja, Banjac, Nebojša, Ušćumlić, Gordana, "Chromatographic and computational screening of anisotropic lipophilicity and pharmacokinetics of newly synthesized 1-aryl-3-ethyl-3-methylsuccinimides" in Computational Biology and Chemistry, 84 (2020),
https://doi.org/10.1016/j.compbiolchem.2019.107161 . .

TY  - JOUR
AU  - Kovačević, Strahinja
AU  - Karadžić Banjac, Milica
AU  - Milošević, Nataša
AU  - Ćurčić, Jelena
AU  - Marjanović, Dunja
AU  - Todorović, Nemanja
AU  - Krmar, Jovana
AU  - Podunavac-Kuzmanović, Sanja
AU  - Banjac, Nebojša
AU  - Ušćumlić, Gordana
PY  - 2020
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5886
AB  - Numerous structurally different amides and imides including succinimide derivatives exhibit diverse bioactive potential. The development of new compounds requires rationalization in the design in or- der to provide structural changes that guarantee favorable physico-chemical properties, pharmacological activity and safety. In the present research, a comprehensive study with comparison of the chromato- graphic lipophilicity and other physico-chemical properties of five groups of 1-arylsuccinimide derivatives was conducted. The chemometric analysis of their physico-chemical properties was carried out by us- ing unsupervised (hierarchical cluster analysis and principal component analysis) and supervised pattern recognition methods (linear discriminant analysis), while the correlations between the in silico molecular features and chromatographic lipophilicity were examined applying linear and non-linear Quantitative Structure–Retention Relationship (QSRR) approaches. The main aim of the conducted research was to determine similarities and dissimilarities among the studied 1-arylsuccinimides, to point out the molec- ular features which have significant influence on their lipophilicity, as well as to establish high-quality QSRR models which can be used in prediction of chromatographic lipophilicity of structurally similar 1-arylsuccinimides. This study is a continuation of analysis and determination of the physico-chemical properties of 1-arylsuccinimides which could be important guidelines in further in vitro and eventually in vivo studies of their biological potential.
PB  - Elsevier B.V.
T2  - Journal of Chromatography A
T1  - Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents
VL  - 1628
DO  - 10.1016/j.chroma.2020.461439
ER  - 

@article{
author = "Kovačević, Strahinja and Karadžić Banjac, Milica and Milošević, Nataša and Ćurčić, Jelena and Marjanović, Dunja and Todorović, Nemanja and Krmar, Jovana and Podunavac-Kuzmanović, Sanja and Banjac, Nebojša and Ušćumlić, Gordana",
year = "2020",
abstract = "Numerous structurally different amides and imides including succinimide derivatives exhibit diverse bioactive potential. The development of new compounds requires rationalization in the design in or- der to provide structural changes that guarantee favorable physico-chemical properties, pharmacological activity and safety. In the present research, a comprehensive study with comparison of the chromato- graphic lipophilicity and other physico-chemical properties of five groups of 1-arylsuccinimide derivatives was conducted. The chemometric analysis of their physico-chemical properties was carried out by us- ing unsupervised (hierarchical cluster analysis and principal component analysis) and supervised pattern recognition methods (linear discriminant analysis), while the correlations between the in silico molecular features and chromatographic lipophilicity were examined applying linear and non-linear Quantitative Structure–Retention Relationship (QSRR) approaches. The main aim of the conducted research was to determine similarities and dissimilarities among the studied 1-arylsuccinimides, to point out the molec- ular features which have significant influence on their lipophilicity, as well as to establish high-quality QSRR models which can be used in prediction of chromatographic lipophilicity of structurally similar 1-arylsuccinimides. This study is a continuation of analysis and determination of the physico-chemical properties of 1-arylsuccinimides which could be important guidelines in further in vitro and eventually in vivo studies of their biological potential.",
publisher = "Elsevier B.V.",
journal = "Journal of Chromatography A",
title = "Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents",
volume = "1628",
doi = "10.1016/j.chroma.2020.461439"
}

Kovačević, S., Karadžić Banjac, M., Milošević, N., Ćurčić, J., Marjanović, D., Todorović, N., Krmar, J., Podunavac-Kuzmanović, S., Banjac, N.,& Ušćumlić, G.. (2020). Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents. in Journal of Chromatography A
Elsevier B.V.., 1628.
https://doi.org/10.1016/j.chroma.2020.461439

Kovačević S, Karadžić Banjac M, Milošević N, Ćurčić J, Marjanović D, Todorović N, Krmar J, Podunavac-Kuzmanović S, Banjac N, Ušćumlić G. Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents. in Journal of Chromatography A. 2020;1628.
doi:10.1016/j.chroma.2020.461439 .

Kovačević, Strahinja, Karadžić Banjac, Milica, Milošević, Nataša, Ćurčić, Jelena, Marjanović, Dunja, Todorović, Nemanja, Krmar, Jovana, Podunavac-Kuzmanović, Sanja, Banjac, Nebojša, Ušćumlić, Gordana, "Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents" in Journal of Chromatography A, 1628 (2020),
https://doi.org/10.1016/j.chroma.2020.461439 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Radovanović, Lidija D.
AU  - Božić, Bojan Đ.
AU  - Božić Nedeljković, Biljana Đ.
AU  - Vitnik, Vesna D.
AU  - Vitnik, Željko J.
AU  - Rogan, Jelena R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana S.
AU  - Trišović, Nemanja P.
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4324
AB  - Two series of cycloalkanespiro-5-hydantoins, namely cyclo-hexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV-Vis, H-1 and C-13 NMR spectroscopy and X-ray crystallography. Regarding their structure-activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N-H center dot center dot center dot center dot O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, OFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV-Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety
EP  - 62
SP  - 48
VL  - 1180
DO  - 10.1016/j.molstruc.2018.11.071
ER  - 

@article{
author = "Lazić, Anita M. and Radovanović, Lidija D. and Božić, Bojan Đ. and Božić Nedeljković, Biljana Đ. and Vitnik, Vesna D. and Vitnik, Željko J. and Rogan, Jelena R. and Valentić, Nataša V. and Ušćumlić, Gordana S. and Trišović, Nemanja P.",
year = "2019",
abstract = "Two series of cycloalkanespiro-5-hydantoins, namely cyclo-hexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV-Vis, H-1 and C-13 NMR spectroscopy and X-ray crystallography. Regarding their structure-activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N-H center dot center dot center dot center dot O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, OFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV-Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety",
pages = "62-48",
volume = "1180",
doi = "10.1016/j.molstruc.2018.11.071"
}

Lazić, A. M., Radovanović, L. D., Božić, B. Đ., Božić Nedeljković, B. Đ., Vitnik, V. D., Vitnik, Ž. J., Rogan, J. R., Valentić, N. V., Ušćumlić, G. S.,& Trišović, N. P.. (2019). Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 1180, 48-62.
https://doi.org/10.1016/j.molstruc.2018.11.071

Lazić AM, Radovanović LD, Božić BĐ, Božić Nedeljković BĐ, Vitnik VD, Vitnik ŽJ, Rogan JR, Valentić NV, Ušćumlić GS, Trišović NP. Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure. 2019;1180:48-62.
doi:10.1016/j.molstruc.2018.11.071 .

Lazić, Anita M., Radovanović, Lidija D., Božić, Bojan Đ., Božić Nedeljković, Biljana Đ., Vitnik, Vesna D., Vitnik, Željko J., Rogan, Jelena R., Valentić, Nataša V., Ušćumlić, Gordana S., Trišović, Nemanja P., "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety" in Journal of Molecular Structure, 1180 (2019):48-62,
https://doi.org/10.1016/j.molstruc.2018.11.071 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Radovanović, Lidija D.
AU  - Božić, Bojan Đ.
AU  - Božić Nedeljković, Biljana Đ.
AU  - Vitnik, Vesna D.
AU  - Vitnik, Željko J.
AU  - Rogan, Jelena R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana S.
AU  - Trišović, Nemanja P.
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5038
AB  - Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1 H and 13 C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.
PB  - Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety
EP  - 62
SP  - 48
VL  - 1180
DO  - 10.1016/j.molstruc.2018.11.071
ER  - 

@article{
author = "Lazić, Anita M. and Radovanović, Lidija D. and Božić, Bojan Đ. and Božić Nedeljković, Biljana Đ. and Vitnik, Vesna D. and Vitnik, Željko J. and Rogan, Jelena R. and Valentić, Nataša V. and Ušćumlić, Gordana S. and Trišović, Nemanja P.",
year = "2019",
abstract = "Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1 H and 13 C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.",
publisher = "Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety",
pages = "62-48",
volume = "1180",
doi = "10.1016/j.molstruc.2018.11.071"
}

Lazić, A. M., Radovanović, L. D., Božić, B. Đ., Božić Nedeljković, B. Đ., Vitnik, V. D., Vitnik, Ž. J., Rogan, J. R., Valentić, N. V., Ušćumlić, G. S.,& Trišović, N. P.. (2019). Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure
Elsevier B.V.., 1180, 48-62.
https://doi.org/10.1016/j.molstruc.2018.11.071

Lazić AM, Radovanović LD, Božić BĐ, Božić Nedeljković BĐ, Vitnik VD, Vitnik ŽJ, Rogan JR, Valentić NV, Ušćumlić GS, Trišović NP. Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure. 2019;1180:48-62.
doi:10.1016/j.molstruc.2018.11.071 .

Lazić, Anita M., Radovanović, Lidija D., Božić, Bojan Đ., Božić Nedeljković, Biljana Đ., Vitnik, Vesna D., Vitnik, Željko J., Rogan, Jelena R., Valentić, Nataša V., Ušćumlić, Gordana S., Trišović, Nemanja P., "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety" in Journal of Molecular Structure, 1180 (2019):48-62,
https://doi.org/10.1016/j.molstruc.2018.11.071 . .

TY  - JOUR
AU  - Lazić, Anita
AU  - Mandić, Željko D.
AU  - Valentić, Nataša
AU  - Ušćumlić, Gordana
AU  - Trišović, Nemanja
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4266
AB  - To create new anticonvulsant drugs, two series of spirohydantoins derived from beta-tetralone bearing a 4-substituted benzyl group (1a-1g) or a 2-(4-substituted phenyl)-2-oxoethyl group (2a-2f) in position 3 of the hydantoin ring were synthesized. The chemical structure of these compounds was confirmed by determination of the melting point, elemental analysis and FT-IR, H-1 NMR, C-13 NMR and UV-Vis spectroscopic methods. Effects of the substituents in the benzyl moiety on the shift of the absorption maxima of compounds 1a-1g and 2a-2f were analyzed using the Hammett's equation. Namely, a split in the Hammett plot at the parent compounds 1a and 2a revealed different electronic transitions within the molecules with the electron-donating substituents from those bearing the electron-accepting substituents, thus the electron-accepting effect on the shift of the absorption maxima being considerably stronger. The influence of the chemical structure on the pharmacokinetically relevant properties of the investigated hydantoin derivatives was evaluated using the Lipinski's rule of five, Veber, Egan and Ghose's empirical criteria, as well as different in silico methods. When compared to phenytoin (5,5-diphenylhydantoin) as the referent drug, compounds with a halogen or electron-donating substituent are expected to possess better intestinal absorption and passage through the blood-brain barrier. Depending on the nature of the substituent present in the benzyl moiety, compounds 1a-1g and 2a-2f can be potent activators/inhibitors of some cytochrome P450 izoenzymes including CYP1A2, CYP2C19 and CYP2C9. Regarding biological activity profile, compounds with the electron-accepting substituents are likely to reveal the pharmacological potential similar to that of phenytoin, while those bearing electron-donating substituents are predicted to have the antimigrenic activity. All compounds were found to bear a low risk of being mutagenic or tumorigenic. The calculated molecular descriptors indicate that the investigated compounds fulfill necessary empirical criteria which qualify them as interesting drug candidates.
PB  - Savez hemijskih inženjera, Beograd
T2  - Hemijska industrija
T1  - New spirohydantoins derived from beta-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie
EP  - 92
IS  - 2
SP  - 79
VL  - 73
DO  - 10.2298/HEMIND181203007L
ER  - 

@article{
author = "Lazić, Anita and Mandić, Željko D. and Valentić, Nataša and Ušćumlić, Gordana and Trišović, Nemanja",
year = "2019",
abstract = "To create new anticonvulsant drugs, two series of spirohydantoins derived from beta-tetralone bearing a 4-substituted benzyl group (1a-1g) or a 2-(4-substituted phenyl)-2-oxoethyl group (2a-2f) in position 3 of the hydantoin ring were synthesized. The chemical structure of these compounds was confirmed by determination of the melting point, elemental analysis and FT-IR, H-1 NMR, C-13 NMR and UV-Vis spectroscopic methods. Effects of the substituents in the benzyl moiety on the shift of the absorption maxima of compounds 1a-1g and 2a-2f were analyzed using the Hammett's equation. Namely, a split in the Hammett plot at the parent compounds 1a and 2a revealed different electronic transitions within the molecules with the electron-donating substituents from those bearing the electron-accepting substituents, thus the electron-accepting effect on the shift of the absorption maxima being considerably stronger. The influence of the chemical structure on the pharmacokinetically relevant properties of the investigated hydantoin derivatives was evaluated using the Lipinski's rule of five, Veber, Egan and Ghose's empirical criteria, as well as different in silico methods. When compared to phenytoin (5,5-diphenylhydantoin) as the referent drug, compounds with a halogen or electron-donating substituent are expected to possess better intestinal absorption and passage through the blood-brain barrier. Depending on the nature of the substituent present in the benzyl moiety, compounds 1a-1g and 2a-2f can be potent activators/inhibitors of some cytochrome P450 izoenzymes including CYP1A2, CYP2C19 and CYP2C9. Regarding biological activity profile, compounds with the electron-accepting substituents are likely to reveal the pharmacological potential similar to that of phenytoin, while those bearing electron-donating substituents are predicted to have the antimigrenic activity. All compounds were found to bear a low risk of being mutagenic or tumorigenic. The calculated molecular descriptors indicate that the investigated compounds fulfill necessary empirical criteria which qualify them as interesting drug candidates.",
publisher = "Savez hemijskih inženjera, Beograd",
journal = "Hemijska industrija",
title = "New spirohydantoins derived from beta-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie",
pages = "92-79",
number = "2",
volume = "73",
doi = "10.2298/HEMIND181203007L"
}

Lazić, A., Mandić, Ž. D., Valentić, N., Ušćumlić, G.,& Trišović, N.. (2019). New spirohydantoins derived from beta-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie. in Hemijska industrija
Savez hemijskih inženjera, Beograd., 73(2), 79-92.
https://doi.org/10.2298/HEMIND181203007L

Lazić A, Mandić ŽD, Valentić N, Ušćumlić G, Trišović N. New spirohydantoins derived from beta-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie. in Hemijska industrija. 2019;73(2):79-92.
doi:10.2298/HEMIND181203007L .

Lazić, Anita, Mandić, Željko D., Valentić, Nataša, Ušćumlić, Gordana, Trišović, Nemanja, "New spirohydantoins derived from beta-tetralone: design, synthesis and evaluation of their pharmacokinetically relevant propertie" in Hemijska industrija, 73, no. 2 (2019):79-92,
https://doi.org/10.2298/HEMIND181203007L . .

TY  - JOUR
AU  - Petković-Cvetković, Jelena
AU  - Božić, Bojan
AU  - Banjac, Nebojša
AU  - Lađarević, Jelena
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Valentić, Nataša
AU  - Ušćumlić, Gordana
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4267
AB  - Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), H-1 and C-13 nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed.
PB  - Savez hemijskih inženjera, Beograd
T2  - Hemijska industrija
T1  - Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents
EP  - 137
IS  - 2
SP  - 125
VL  - 73
DO  - 10.2298/HEMIND190214011P
ER  - 

@article{
author = "Petković-Cvetković, Jelena and Božić, Bojan and Banjac, Nebojša and Lađarević, Jelena and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša and Ušćumlić, Gordana",
year = "2019",
abstract = "Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), H-1 and C-13 nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed.",
publisher = "Savez hemijskih inženjera, Beograd",
journal = "Hemijska industrija",
title = "Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents",
pages = "137-125",
number = "2",
volume = "73",
doi = "10.2298/HEMIND190214011P"
}

Petković-Cvetković, J., Božić, B., Banjac, N., Lađarević, J., Vitnik, V., Vitnik, Ž., Valentić, N.,& Ušćumlić, G.. (2019). Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents. in Hemijska industrija
Savez hemijskih inženjera, Beograd., 73(2), 125-137.
https://doi.org/10.2298/HEMIND190214011P

Petković-Cvetković J, Božić B, Banjac N, Lađarević J, Vitnik V, Vitnik Ž, Valentić N, Ušćumlić G. Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents. in Hemijska industrija. 2019;73(2):125-137.
doi:10.2298/HEMIND190214011P .

Petković-Cvetković, Jelena, Božić, Bojan, Banjac, Nebojša, Lađarević, Jelena, Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša, Ušćumlić, Gordana, "Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents" in Hemijska industrija, 73, no. 2 (2019):125-137,
https://doi.org/10.2298/HEMIND190214011P . .

TY  - JOUR
AU  - Petković-Cvetković, Jelena
AU  - Božić, Bojan
AU  - Banjac, Nebojša
AU  - Petrović, Jovana
AU  - Soković, Marina
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Ušćumlić, Gordana
AU  - Valentić, Nataša
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4309
AB  - In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives
EP  - 156
SP  - 148
VL  - 1181
DO  - 10.1016/j.molstruc.2018.12.083
ER  - 

@article{
author = "Petković-Cvetković, Jelena and Božić, Bojan and Banjac, Nebojša and Petrović, Jovana and Soković, Marina and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana and Valentić, Nataša",
year = "2019",
abstract = "In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives",
pages = "156-148",
volume = "1181",
doi = "10.1016/j.molstruc.2018.12.083"
}

Petković-Cvetković, J., Božić, B., Banjac, N., Petrović, J., Soković, M., Vitnik, V., Vitnik, Ž., Ušćumlić, G.,& Valentić, N.. (2019). Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 1181, 148-156.
https://doi.org/10.1016/j.molstruc.2018.12.083

Petković-Cvetković J, Božić B, Banjac N, Petrović J, Soković M, Vitnik V, Vitnik Ž, Ušćumlić G, Valentić N. Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure. 2019;1181:148-156.
doi:10.1016/j.molstruc.2018.12.083 .

Petković-Cvetković, Jelena, Božić, Bojan, Banjac, Nebojša, Petrović, Jovana, Soković, Marina, Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, Valentić, Nataša, "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives" in Journal of Molecular Structure, 1181 (2019):148-156,
https://doi.org/10.1016/j.molstruc.2018.12.083 . .

TY  - CONF
AU  - Lazić, Anita M.
AU  - Mandić, Željko
AU  - Trišović, Nemanja P.
AU  - Ušćumlić, Gordana S.
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6789
AB  - Among the diverse pharmacological activity reported for spirohydantoin and the closely related spirosuccinimides, their anticonvulsant and antiproliferative activities are commonly encountered. Of all cyclic ureide derivatives, Phenytoin (5,5-diphenylhydantoin) is one of the well-known commercially available anticonvulsants, which is also widely used as an antiarrhythmic agent. However, the clinical use of 5,5-diphenylhydantoin is limited by its central nervous adverse effects in addition to a wide variety of drug interactions [1]. With the aim of developing new analogs with a more efficient therapeutic effect, a series of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-diones, have been synthesized, characterized by melting points, FT-IR, 1H and 13C NMR spectroscopic techniques, and evaluated for anticonvulsant activity. The objective of the present investigation is to identify the pharmacological impact of the spirocyclic attachment of a semi-rigid tetralin residue at C-5 of the imidazolidine-2,4-dione ring and to explore the effect of substitution at N-3 on anticonvulsant activity.
PB  - Beograd : Serbian Chemical Society
C3  - Book of Abstracts / Sixth Conference of Young Chemists of Serbia, Belgrade, 27th October 2018
T1  - Synthesis and characterization of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-dione derivatives as potential anticonvulsant agents
T1  - Sinteza i karakterizacija 1-(4-supstituisanih benzil)-3’,4’-dihidro-2’H-spiro[imidazolidin-4,1’-naftalen]-2,5-diona potencijalnih antikonvulzivnih agenasa
SP  - 56
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6789
ER  - 

@conference{
author = "Lazić, Anita M. and Mandić, Željko and Trišović, Nemanja P. and Ušćumlić, Gordana S.",
year = "2018",
abstract = "Among the diverse pharmacological activity reported for spirohydantoin and the closely related spirosuccinimides, their anticonvulsant and antiproliferative activities are commonly encountered. Of all cyclic ureide derivatives, Phenytoin (5,5-diphenylhydantoin) is one of the well-known commercially available anticonvulsants, which is also widely used as an antiarrhythmic agent. However, the clinical use of 5,5-diphenylhydantoin is limited by its central nervous adverse effects in addition to a wide variety of drug interactions [1]. With the aim of developing new analogs with a more efficient therapeutic effect, a series of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-diones, have been synthesized, characterized by melting points, FT-IR, 1H and 13C NMR spectroscopic techniques, and evaluated for anticonvulsant activity. The objective of the present investigation is to identify the pharmacological impact of the spirocyclic attachment of a semi-rigid tetralin residue at C-5 of the imidazolidine-2,4-dione ring and to explore the effect of substitution at N-3 on anticonvulsant activity.",
publisher = "Beograd : Serbian Chemical Society",
journal = "Book of Abstracts / Sixth Conference of Young Chemists of Serbia, Belgrade, 27th October 2018",
title = "Synthesis and characterization of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-dione derivatives as potential anticonvulsant agents, Sinteza i karakterizacija 1-(4-supstituisanih benzil)-3’,4’-dihidro-2’H-spiro[imidazolidin-4,1’-naftalen]-2,5-diona potencijalnih antikonvulzivnih agenasa",
pages = "56",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6789"
}

Lazić, A. M., Mandić, Ž., Trišović, N. P.,& Ušćumlić, G. S.. (2018). Synthesis and characterization of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-dione derivatives as potential anticonvulsant agents. in Book of Abstracts / Sixth Conference of Young Chemists of Serbia, Belgrade, 27th October 2018
Beograd : Serbian Chemical Society., 56.
https://hdl.handle.net/21.15107/rcub_technorep_6789

Lazić AM, Mandić Ž, Trišović NP, Ušćumlić GS. Synthesis and characterization of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-dione derivatives as potential anticonvulsant agents. in Book of Abstracts / Sixth Conference of Young Chemists of Serbia, Belgrade, 27th October 2018. 2018;:56.
https://hdl.handle.net/21.15107/rcub_technorep_6789 .

Lazić, Anita M., Mandić, Željko, Trišović, Nemanja P., Ušćumlić, Gordana S., "Synthesis and characterization of 1-(4-substitutedbenzyl)-3’,4’-dihydro-2’H-spiro[imidazolidine-4,1’-naphtalene]-2,5-dione derivatives as potential anticonvulsant agents" in Book of Abstracts / Sixth Conference of Young Chemists of Serbia, Belgrade, 27th October 2018 (2018):56,
https://hdl.handle.net/21.15107/rcub_technorep_6789 .

TY  - JOUR
AU  - Valentić, Nataša
AU  - Lađarević, Jelena
AU  - Božić, Bojan
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3834
AB  - Eight 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones were synthesized by reaction of benzoylacetone and arendiazonium salt, followed by condensation with cyanoacetamide. Absorption spectra of all azo pyridone dyes were recorded in twelve protic and aprotic solvents in the range of 200-600 nm. A simple Hammett equation was used to study the effect of the substituents on the absorption spectra of these azo dyes. The solute-solvent interactions were clarified on the basis of linear solvation energy relationships concept proposed by Kamlet and Taft. The results showed that the solvent effects on the absorption spectra of the investigated azo dyes were very complex and strongly dependent on the nature of the substituents on the phenylazo group.
AB  - Osam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona je sintetizovano reakcijom benzoilacetona i arendiazonijumove soli, i kondenzacijom nastalog proizvoda sa cijano-acetamidom. Apsorpcioni spektri dobijenih arilazo piridonskih boja su snimljeni u dvanaest protičnih i aprotičnih rastvarača u opsegu od 200-600 nm. Za proučavanje uticaja supstituenata na apsorpcione spektre ispitivanih azo boja korišćena je prosta ametova jednačina. Interakcije rastvorak-rastvarač su razjašnjene na osnovu koncepta linearne korelacije energije solvatacije, koji su predložili Kamlet i Taft. Rezultati pokazuju da su efekti rastvarača na apsorpcione spektre istraženih azo boja veoma kompleksni i jako zavise od prirode supstituenata na fenilazo grupi.
PB  - Engineering Society for Corrosion, Belgrade, Serbia
T2  - Zaštita materijala
T1  - Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones
T1  - Solvatohromizam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona
EP  - 125
IS  - 1
SP  - 117
VL  - 59
DO  - 10.5937/ZasMat1801119V
ER  - 

@article{
author = "Valentić, Nataša and Lađarević, Jelena and Božić, Bojan and Mijin, Dušan and Ušćumlić, Gordana",
year = "2018",
abstract = "Eight 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones were synthesized by reaction of benzoylacetone and arendiazonium salt, followed by condensation with cyanoacetamide. Absorption spectra of all azo pyridone dyes were recorded in twelve protic and aprotic solvents in the range of 200-600 nm. A simple Hammett equation was used to study the effect of the substituents on the absorption spectra of these azo dyes. The solute-solvent interactions were clarified on the basis of linear solvation energy relationships concept proposed by Kamlet and Taft. The results showed that the solvent effects on the absorption spectra of the investigated azo dyes were very complex and strongly dependent on the nature of the substituents on the phenylazo group., Osam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona je sintetizovano reakcijom benzoilacetona i arendiazonijumove soli, i kondenzacijom nastalog proizvoda sa cijano-acetamidom. Apsorpcioni spektri dobijenih arilazo piridonskih boja su snimljeni u dvanaest protičnih i aprotičnih rastvarača u opsegu od 200-600 nm. Za proučavanje uticaja supstituenata na apsorpcione spektre ispitivanih azo boja korišćena je prosta ametova jednačina. Interakcije rastvorak-rastvarač su razjašnjene na osnovu koncepta linearne korelacije energije solvatacije, koji su predložili Kamlet i Taft. Rezultati pokazuju da su efekti rastvarača na apsorpcione spektre istraženih azo boja veoma kompleksni i jako zavise od prirode supstituenata na fenilazo grupi.",
publisher = "Engineering Society for Corrosion, Belgrade, Serbia",
journal = "Zaštita materijala",
title = "Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones, Solvatohromizam 5-(4-supstituisanih arilazo)-4-fenil-6-metil-3-cijano-2-piridona",
pages = "125-117",
number = "1",
volume = "59",
doi = "10.5937/ZasMat1801119V"
}

Valentić, N., Lađarević, J., Božić, B., Mijin, D.,& Ušćumlić, G.. (2018). Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones. in Zaštita materijala
Engineering Society for Corrosion, Belgrade, Serbia., 59(1), 117-125.
https://doi.org/10.5937/ZasMat1801119V

Valentić N, Lađarević J, Božić B, Mijin D, Ušćumlić G. Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones. in Zaštita materijala. 2018;59(1):117-125.
doi:10.5937/ZasMat1801119V .

Valentić, Nataša, Lađarević, Jelena, Božić, Bojan, Mijin, Dušan, Ušćumlić, Gordana, "Solvatochromism of 5-(4-substituted arylazo)-4-phenyl-6-methyl-3-cyano-2-pyridones" in Zaštita materijala, 59, no. 1 (2018):117-125,
https://doi.org/10.5937/ZasMat1801119V . .

TY  - JOUR
AU  - Božić, Bojan
AU  - Lović, Jelena
AU  - Banjac, Nebojša
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
AU  - Avramov-Ivić, Milka
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3871
AB  - A series of succinimide derivatives were studied using the cyclic and square wave voltammetry. Density function theory was used in order to determinate which of the structural parameters influence the electrochemical activity. The quantum chemical calculations of the investigated succinimides were linked with the experimental electrochemical data and used to propose the oxidation mechanism. The most active among studied succinimides is 1,3-diphenylsuccinimide. The results obtained from the cyclic and square wave voltammetry and quantum chemical calculations indicate that the investigated compounds undergo oxidation by irreversible, diffusion controlled process including transfer of 1e(-) and 1 proton. The voltammetric and DFT results signify that the mechanism of electrochemical oxidation of all compounds involve the conversion of carbonyl-methyne-phenyl segment or methylene group in free radical. This conversion proceeds by the loss of one proton one electron process.
PB  - Electrochemical Science Group, Beograd
T2  - International Journal of Electrochemical Science
T1  - Voltammetric and Quantum Investigation of Selected Succinimides
EP  - 4297
IS  - 5
SP  - 4285
VL  - 13
DO  - 10.20964/2018.05.54
ER  - 

@article{
author = "Božić, Bojan and Lović, Jelena and Banjac, Nebojša and Vitnik, Željko and Vitnik, Vesna and Mijin, Dušan and Ušćumlić, Gordana and Avramov-Ivić, Milka",
year = "2018",
abstract = "A series of succinimide derivatives were studied using the cyclic and square wave voltammetry. Density function theory was used in order to determinate which of the structural parameters influence the electrochemical activity. The quantum chemical calculations of the investigated succinimides were linked with the experimental electrochemical data and used to propose the oxidation mechanism. The most active among studied succinimides is 1,3-diphenylsuccinimide. The results obtained from the cyclic and square wave voltammetry and quantum chemical calculations indicate that the investigated compounds undergo oxidation by irreversible, diffusion controlled process including transfer of 1e(-) and 1 proton. The voltammetric and DFT results signify that the mechanism of electrochemical oxidation of all compounds involve the conversion of carbonyl-methyne-phenyl segment or methylene group in free radical. This conversion proceeds by the loss of one proton one electron process.",
publisher = "Electrochemical Science Group, Beograd",
journal = "International Journal of Electrochemical Science",
title = "Voltammetric and Quantum Investigation of Selected Succinimides",
pages = "4297-4285",
number = "5",
volume = "13",
doi = "10.20964/2018.05.54"
}

Božić, B., Lović, J., Banjac, N., Vitnik, Ž., Vitnik, V., Mijin, D., Ušćumlić, G.,& Avramov-Ivić, M.. (2018). Voltammetric and Quantum Investigation of Selected Succinimides. in International Journal of Electrochemical Science
Electrochemical Science Group, Beograd., 13(5), 4285-4297.
https://doi.org/10.20964/2018.05.54

Božić B, Lović J, Banjac N, Vitnik Ž, Vitnik V, Mijin D, Ušćumlić G, Avramov-Ivić M. Voltammetric and Quantum Investigation of Selected Succinimides. in International Journal of Electrochemical Science. 2018;13(5):4285-4297.
doi:10.20964/2018.05.54 .

Božić, Bojan, Lović, Jelena, Banjac, Nebojša, Vitnik, Željko, Vitnik, Vesna, Mijin, Dušan, Ušćumlić, Gordana, Avramov-Ivić, Milka, "Voltammetric and Quantum Investigation of Selected Succinimides" in International Journal of Electrochemical Science, 13, no. 5 (2018):4285-4297,
https://doi.org/10.20964/2018.05.54 . .

TY  - JOUR
AU  - Mijin, Dušan
AU  - Božić, Bojan
AU  - Lađarević, Jelena
AU  - Matović, Luka
AU  - Ušćumlić, Gordana
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3945
AB  - Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid-base equilibrium exists. Excellent agreement between computational and experimental UV-visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted over the optimised geometry to lighten the reactivity of the investigated molecule.
PB  - Wiley, Hoboken
T2  - Coloration Technology
T1  - Solvatochromism and quantum mechanical investigation of disazo pyridone dye
EP  - 490
IS  - 6
SP  - 478
VL  - 134
DO  - 10.1111/cote.12369
ER  - 

@article{
author = "Mijin, Dušan and Božić, Bojan and Lađarević, Jelena and Matović, Luka and Ušćumlić, Gordana and Vitnik, Vesna and Vitnik, Željko",
year = "2018",
abstract = "Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid-base equilibrium exists. Excellent agreement between computational and experimental UV-visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted over the optimised geometry to lighten the reactivity of the investigated molecule.",
publisher = "Wiley, Hoboken",
journal = "Coloration Technology",
title = "Solvatochromism and quantum mechanical investigation of disazo pyridone dye",
pages = "490-478",
number = "6",
volume = "134",
doi = "10.1111/cote.12369"
}

Mijin, D., Božić, B., Lađarević, J., Matović, L., Ušćumlić, G., Vitnik, V.,& Vitnik, Ž.. (2018). Solvatochromism and quantum mechanical investigation of disazo pyridone dye. in Coloration Technology
Wiley, Hoboken., 134(6), 478-490.
https://doi.org/10.1111/cote.12369

Mijin D, Božić B, Lađarević J, Matović L, Ušćumlić G, Vitnik V, Vitnik Ž. Solvatochromism and quantum mechanical investigation of disazo pyridone dye. in Coloration Technology. 2018;134(6):478-490.
doi:10.1111/cote.12369 .

Mijin, Dušan, Božić, Bojan, Lađarević, Jelena, Matović, Luka, Ušćumlić, Gordana, Vitnik, Vesna, Vitnik, Željko, "Solvatochromism and quantum mechanical investigation of disazo pyridone dye" in Coloration Technology, 134, no. 6 (2018):478-490,
https://doi.org/10.1111/cote.12369 . .

TY  - JOUR
AU  - Mirković, Jelena
AU  - Božić, Bojan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3972
AB  - Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (- stacking and lone pair- interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern.
PB  - Wiley, Hoboken
T2  - Coloration Technology
T1  - Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones
EP  - 43
IS  - 1
SP  - 33
VL  - 134
DO  - 10.1111/cote.12321
ER  - 

@article{
author = "Mirković, Jelena and Božić, Bojan and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena and Poleti, Dejan and Ušćumlić, Gordana and Mijin, Dušan",
year = "2018",
abstract = "Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (- stacking and lone pair- interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern.",
publisher = "Wiley, Hoboken",
journal = "Coloration Technology",
title = "Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones",
pages = "43-33",
number = "1",
volume = "134",
doi = "10.1111/cote.12321"
}

Mirković, J., Božić, B., Vitnik, V., Vitnik, Ž., Rogan, J., Poleti, D., Ušćumlić, G.,& Mijin, D.. (2018). Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. in Coloration Technology
Wiley, Hoboken., 134(1), 33-43.
https://doi.org/10.1111/cote.12321

Mirković J, Božić B, Vitnik V, Vitnik Ž, Rogan J, Poleti D, Ušćumlić G, Mijin D. Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. in Coloration Technology. 2018;134(1):33-43.
doi:10.1111/cote.12321 .

Mirković, Jelena, Božić, Bojan, Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena, Poleti, Dejan, Ušćumlić, Gordana, Mijin, Dušan, "Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones" in Coloration Technology, 134, no. 1 (2018):33-43,
https://doi.org/10.1111/cote.12321 . .

TY  - JOUR
AU  - Babić, Marija
AU  - Božić, Bojan
AU  - Božić, Biljana
AU  - Ušćumlić, Gordana
AU  - Tomić, Simonida
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3979
AB  - The discovery of novel biodegradable biomaterials able to support and control cellular activity as well as development of an enhanced and efficient method for their fabrication, are of paramount importance in the field of tissue engineering. This study highlights the design of novel degradable hydrogels based on gelatin and hydroxyethyl (meth)acrylates using the innovative combined two-step sequential microwave-assisted and UV photo-polymerization technique. Chemical composition, morphology, swelling capacity and degradation rate of the synthesized hydrogels were evaluated by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), swelling and weight loss measurements. As an initial step for evaluation of performance of the hydrogels in the biological environment, the in vitro biocompatibility of these hydrogels, was evaluated using L929 mouse fibroblasts. Obtained results demonstrated that the hydrogels possess a porous morphology with interconnected pores, 50% in vitro degradation after 7 months, and satisfied biocompatibility on L929 fibroblast cells. These unique performances of the hydrogels make them promising candidates for in vivo evaluation in clinical studies aiming at tissue regeneration.
PB  - Elsevier Science Bv, Amsterdam
T2  - Materials Letters
T1  - The innovative combined microwave-assisted and photo-polymerization technique for synthesis of the novel degradable hydroxyethyl (meth)acrylate/gelatin based scaffolds
EP  - 240
SP  - 236
VL  - 213
DO  - 10.1016/j.matlet.2017.11.087
ER  - 

@article{
author = "Babić, Marija and Božić, Bojan and Božić, Biljana and Ušćumlić, Gordana and Tomić, Simonida",
year = "2018",
abstract = "The discovery of novel biodegradable biomaterials able to support and control cellular activity as well as development of an enhanced and efficient method for their fabrication, are of paramount importance in the field of tissue engineering. This study highlights the design of novel degradable hydrogels based on gelatin and hydroxyethyl (meth)acrylates using the innovative combined two-step sequential microwave-assisted and UV photo-polymerization technique. Chemical composition, morphology, swelling capacity and degradation rate of the synthesized hydrogels were evaluated by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), swelling and weight loss measurements. As an initial step for evaluation of performance of the hydrogels in the biological environment, the in vitro biocompatibility of these hydrogels, was evaluated using L929 mouse fibroblasts. Obtained results demonstrated that the hydrogels possess a porous morphology with interconnected pores, 50% in vitro degradation after 7 months, and satisfied biocompatibility on L929 fibroblast cells. These unique performances of the hydrogels make them promising candidates for in vivo evaluation in clinical studies aiming at tissue regeneration.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Materials Letters",
title = "The innovative combined microwave-assisted and photo-polymerization technique for synthesis of the novel degradable hydroxyethyl (meth)acrylate/gelatin based scaffolds",
pages = "240-236",
volume = "213",
doi = "10.1016/j.matlet.2017.11.087"
}

Babić, M., Božić, B., Božić, B., Ušćumlić, G.,& Tomić, S.. (2018). The innovative combined microwave-assisted and photo-polymerization technique for synthesis of the novel degradable hydroxyethyl (meth)acrylate/gelatin based scaffolds. in Materials Letters
Elsevier Science Bv, Amsterdam., 213, 236-240.
https://doi.org/10.1016/j.matlet.2017.11.087

Babić M, Božić B, Božić B, Ušćumlić G, Tomić S. The innovative combined microwave-assisted and photo-polymerization technique for synthesis of the novel degradable hydroxyethyl (meth)acrylate/gelatin based scaffolds. in Materials Letters. 2018;213:236-240.
doi:10.1016/j.matlet.2017.11.087 .

Babić, Marija, Božić, Bojan, Božić, Biljana, Ušćumlić, Gordana, Tomić, Simonida, "The innovative combined microwave-assisted and photo-polymerization technique for synthesis of the novel degradable hydroxyethyl (meth)acrylate/gelatin based scaffolds" in Materials Letters, 213 (2018):236-240,
https://doi.org/10.1016/j.matlet.2017.11.087 . .

TY  - JOUR
AU  - Mijin, Dušan
AU  - Božić-Nedeljković, Biljana
AU  - Božić, Bojan
AU  - Kovrlija, Ilijana
AU  - Lađarević, Jelena
AU  - Ušćumlić, Gordana
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4008
AB  - New azo dyes bearing 2-pyridone and benzimidazole moieties were prepared using diazotization of 4-(1H-benzo[d]imidazol-2-yl)aniline and coupling of the obtained diazonium salt with substituted 3-cyano-2-pyridones. Obtained compounds were characterized via UV-Vis, FT-IR, and H-1 and C-13 NMR spectroscopy as well as by elemental analysis data. The UV-Vis spectra of the synthesized dyes were measured in thirteen solvents of different properties at room temperature. Solvatochromism and tautomerism of novel azo dyes were discussed. An MTT (3,4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide) test was performed to prove the biocompatibility of the investigated dyes. The investigated dyes exhibited satisfying antiproliferative activities against both tumor cell lines, MDA-MB-231 and HCT-116, demonstrating the potent capacity for treatment of tumors.
PB  - Scientific Technical Research Council Turkey-Tubitak, Ankara
T2  - Turkish Journal of Chemistry
T1  - Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties
EP  - 907
IS  - 3
SP  - 896
VL  - 42
DO  - 10.3906/kim-1711-97
ER  - 

@article{
author = "Mijin, Dušan and Božić-Nedeljković, Biljana and Božić, Bojan and Kovrlija, Ilijana and Lađarević, Jelena and Ušćumlić, Gordana",
year = "2018",
abstract = "New azo dyes bearing 2-pyridone and benzimidazole moieties were prepared using diazotization of 4-(1H-benzo[d]imidazol-2-yl)aniline and coupling of the obtained diazonium salt with substituted 3-cyano-2-pyridones. Obtained compounds were characterized via UV-Vis, FT-IR, and H-1 and C-13 NMR spectroscopy as well as by elemental analysis data. The UV-Vis spectra of the synthesized dyes were measured in thirteen solvents of different properties at room temperature. Solvatochromism and tautomerism of novel azo dyes were discussed. An MTT (3,4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide) test was performed to prove the biocompatibility of the investigated dyes. The investigated dyes exhibited satisfying antiproliferative activities against both tumor cell lines, MDA-MB-231 and HCT-116, demonstrating the potent capacity for treatment of tumors.",
publisher = "Scientific Technical Research Council Turkey-Tubitak, Ankara",
journal = "Turkish Journal of Chemistry",
title = "Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties",
pages = "907-896",
number = "3",
volume = "42",
doi = "10.3906/kim-1711-97"
}

Mijin, D., Božić-Nedeljković, B., Božić, B., Kovrlija, I., Lađarević, J.,& Ušćumlić, G.. (2018). Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties. in Turkish Journal of Chemistry
Scientific Technical Research Council Turkey-Tubitak, Ankara., 42(3), 896-907.
https://doi.org/10.3906/kim-1711-97

Mijin D, Božić-Nedeljković B, Božić B, Kovrlija I, Lađarević J, Ušćumlić G. Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties. in Turkish Journal of Chemistry. 2018;42(3):896-907.
doi:10.3906/kim-1711-97 .

Mijin, Dušan, Božić-Nedeljković, Biljana, Božić, Bojan, Kovrlija, Ilijana, Lađarević, Jelena, Ušćumlić, Gordana, "Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties" in Turkish Journal of Chemistry, 42, no. 3 (2018):896-907,
https://doi.org/10.3906/kim-1711-97 . .

TY  - CONF
AU  - Lazić, Anita M.
AU  - Radovanović, Lidija D.
AU  - Božić, Biljana Đ.
AU  - Ušćumlić, Gordana S.
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6764
AB  - U okviru proučavanja uticaja strukture na biološku aktivnost derivata cikloalkanspiro-5-hidantoina,
u radu je testirana citotoksičnost novih serija jedinjenja: 3-(4-supstituisanih benzil)-1,3-
-diazaspiro[4.5]dekan-2,4-diona i 3-(4-supstituisanih benzil)-1,3-diazaspiro[4.6] undekan-2,4-
diona. Citotoksična aktivnost određena je MTT testom prema ćelijskoj liniji humanog karcinoma
dojke (MDA-MB-231). Strukturne karakteristike jedinjenja su određene rendgenskom strukturnom
analizom kao i odgovarajućim spektroskopskim metodama. Testirana jedinjenja su pokazala
statistički značajnu antiproliferativnu aktivnost prema ćelijskoj liniji MDA-MB-231 u proučavanom
opsegu koncentracija. Naročito su se istakli derivati koji u okviru svoje strukture sadrže kao
supstituente atome halogena i nitro-grupu. Rezultati su upoređeni sa prethodno određenom
antiproliferativnom aktivnošću za 3-(4-supstituisane benzil)-5,5-difenilhidantoine. Diskutovan je
uticaj strukture na antiproliferativnu aktivnost proučavanih jedinjenja.
AB  - In order to investigate the influence of the structure on the antiproliferative activity of the cycloalkanespiro-5-hydantoine derivatives, the cytotoxity of the new series of compounds: 3-(4- substituted benzyl)-1,3-diazaspiro[4.5]decane-2,4-dione and 3-(4-substituted benzyl)-1,3- -diazaspiro[4.6]undecane-2,4-dione has been tested. Cytotoxic activity was determined by the MTT assay againist the cell line of human breast cancer (MDA-MB-231). The structural characteristics of the compounds are determined by X-ray structural analysis, as well as by appropriate spectroscopic methods. The tested compounds showed statistically significant antiproliferative activity to the MDA-MB-231 cell line in the studied concentration range. Among the most active are derivatives containing as substituents halogen atoms and a nitro group. The results were compared with a predetermined antiproliferative activity for 3-(4-substituted benzil)-5,5- -diphenylhydantoines. The influence of structure on the antiproliferative activity of the studied compounds is also discussed.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi i Knjiga radova / 54. savetovanje Srpskog hemijskog društva i 5. konferencija mladih hemičara Srbije, Beograd 29. i 30. septembar 2017
T1  - Uticaj strukture na antiproliferativnu aktivnost derivata cikloalkanspiro-5-hidantoina
T1  - The influence of the structure on the antiproliferative activity of the cycloalkanespiro-5-hydantoin derivatives
SP  - 103
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6764
ER  - 

@conference{
author = "Lazić, Anita M. and Radovanović, Lidija D. and Božić, Biljana Đ. and Ušćumlić, Gordana S.",
year = "2017",
abstract = "U okviru proučavanja uticaja strukture na biološku aktivnost derivata cikloalkanspiro-5-hidantoina,
u radu je testirana citotoksičnost novih serija jedinjenja: 3-(4-supstituisanih benzil)-1,3-
-diazaspiro[4.5]dekan-2,4-diona i 3-(4-supstituisanih benzil)-1,3-diazaspiro[4.6] undekan-2,4-
diona. Citotoksična aktivnost određena je MTT testom prema ćelijskoj liniji humanog karcinoma
dojke (MDA-MB-231). Strukturne karakteristike jedinjenja su određene rendgenskom strukturnom
analizom kao i odgovarajućim spektroskopskim metodama. Testirana jedinjenja su pokazala
statistički značajnu antiproliferativnu aktivnost prema ćelijskoj liniji MDA-MB-231 u proučavanom
opsegu koncentracija. Naročito su se istakli derivati koji u okviru svoje strukture sadrže kao
supstituente atome halogena i nitro-grupu. Rezultati su upoređeni sa prethodno određenom
antiproliferativnom aktivnošću za 3-(4-supstituisane benzil)-5,5-difenilhidantoine. Diskutovan je
uticaj strukture na antiproliferativnu aktivnost proučavanih jedinjenja., In order to investigate the influence of the structure on the antiproliferative activity of the cycloalkanespiro-5-hydantoine derivatives, the cytotoxity of the new series of compounds: 3-(4- substituted benzyl)-1,3-diazaspiro[4.5]decane-2,4-dione and 3-(4-substituted benzyl)-1,3- -diazaspiro[4.6]undecane-2,4-dione has been tested. Cytotoxic activity was determined by the MTT assay againist the cell line of human breast cancer (MDA-MB-231). The structural characteristics of the compounds are determined by X-ray structural analysis, as well as by appropriate spectroscopic methods. The tested compounds showed statistically significant antiproliferative activity to the MDA-MB-231 cell line in the studied concentration range. Among the most active are derivatives containing as substituents halogen atoms and a nitro group. The results were compared with a predetermined antiproliferative activity for 3-(4-substituted benzil)-5,5- -diphenylhydantoines. The influence of structure on the antiproliferative activity of the studied compounds is also discussed.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi i Knjiga radova / 54. savetovanje Srpskog hemijskog društva i 5. konferencija mladih hemičara Srbije, Beograd 29. i 30. septembar 2017",
title = "Uticaj strukture na antiproliferativnu aktivnost derivata cikloalkanspiro-5-hidantoina, The influence of the structure on the antiproliferative activity of the cycloalkanespiro-5-hydantoin derivatives",
pages = "103",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6764"
}

Lazić, A. M., Radovanović, L. D., Božić, B. Đ.,& Ušćumlić, G. S.. (2017). Uticaj strukture na antiproliferativnu aktivnost derivata cikloalkanspiro-5-hidantoina. in Kratki izvodi i Knjiga radova / 54. savetovanje Srpskog hemijskog društva i 5. konferencija mladih hemičara Srbije, Beograd 29. i 30. septembar 2017
Beograd : Srpsko hemijsko društvo., 103.
https://hdl.handle.net/21.15107/rcub_technorep_6764

Lazić AM, Radovanović LD, Božić BĐ, Ušćumlić GS. Uticaj strukture na antiproliferativnu aktivnost derivata cikloalkanspiro-5-hidantoina. in Kratki izvodi i Knjiga radova / 54. savetovanje Srpskog hemijskog društva i 5. konferencija mladih hemičara Srbije, Beograd 29. i 30. septembar 2017. 2017;:103.
https://hdl.handle.net/21.15107/rcub_technorep_6764 .

Lazić, Anita M., Radovanović, Lidija D., Božić, Biljana Đ., Ušćumlić, Gordana S., "Uticaj strukture na antiproliferativnu aktivnost derivata cikloalkanspiro-5-hidantoina" in Kratki izvodi i Knjiga radova / 54. savetovanje Srpskog hemijskog društva i 5. konferencija mladih hemičara Srbije, Beograd 29. i 30. septembar 2017 (2017):103,
https://hdl.handle.net/21.15107/rcub_technorep_6764 .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Božić, Bojan Ð.
AU  - Vitnik, Vesna D.
AU  - Vitnik, Željko J.
AU  - Rogan, Jelena R.
AU  - Radovanović, Lidija D.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana S.
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3658
AB  - The structure-property relationship of newly synthesized 3-(4-substituted benzyl)-1,3-diazaspiro [4.4] nonane-2,4-diones was studied by experimental and calculated methods. The prepared compounds were characterized by UV-Vis, FT-IR, H-1 NMR and C-13 NMR spectroscopy and elemental analysis. The crystal structure was elucidated by single-crystal X-ray diffraction. The 3-benzy1-1,3-diazaspiro[4.41nonane-2,4-dione crystallizes in triclinic P-1 space group, with two crystallographically independent molecules in the asymmetric unit. Cyclopentane ring adopts an envelope conformation. A three-dimensional crystal packing is governed by hydrogen N-H center dot center dot center dot O bonds, numerous C-H center dot center dot center dot O/N and C-H center dot center dot center dot pi interactions between neighboring molecules. Density functional theory (DFT) calculations with B3LYP and M06-2X methods using 6-311++G(d,p) basis set were performed to provide structural and spectroscopic information. Comparisons between experimental and calculated UV-Vis spectral properties suggest that the monomeric form of the investigated spirohydantoins is dominant in all used solvents. The effects of substituents on the absorption spectra of spirohydantoins are interpreted by correlation of absorption frequencies with Hammett equation. The lipophilicities of the investigated molecules were estimated by calculation of their log P values. Some of the spirohydantoins synthesized in this work, exhibit the lipophilicities comparable to the standard medicine anticonvulsant drug Phenytoin. The results obtained in this investigation afford guidelines for the preparation of new derivatives of spirohydantoin as potential anticonvulsant agents and for better understanding the structure-activity relationship.
PB  - Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study
EP  - 98
SP  - 88
VL  - 1127
DO  - 10.1016/j.molstruc.2016.07.069
ER  - 

@article{
author = "Lazić, Anita M. and Božić, Bojan Ð. and Vitnik, Vesna D. and Vitnik, Željko J. and Rogan, Jelena R. and Radovanović, Lidija D. and Valentić, Nataša V. and Ušćumlić, Gordana S.",
year = "2017",
abstract = "The structure-property relationship of newly synthesized 3-(4-substituted benzyl)-1,3-diazaspiro [4.4] nonane-2,4-diones was studied by experimental and calculated methods. The prepared compounds were characterized by UV-Vis, FT-IR, H-1 NMR and C-13 NMR spectroscopy and elemental analysis. The crystal structure was elucidated by single-crystal X-ray diffraction. The 3-benzy1-1,3-diazaspiro[4.41nonane-2,4-dione crystallizes in triclinic P-1 space group, with two crystallographically independent molecules in the asymmetric unit. Cyclopentane ring adopts an envelope conformation. A three-dimensional crystal packing is governed by hydrogen N-H center dot center dot center dot O bonds, numerous C-H center dot center dot center dot O/N and C-H center dot center dot center dot pi interactions between neighboring molecules. Density functional theory (DFT) calculations with B3LYP and M06-2X methods using 6-311++G(d,p) basis set were performed to provide structural and spectroscopic information. Comparisons between experimental and calculated UV-Vis spectral properties suggest that the monomeric form of the investigated spirohydantoins is dominant in all used solvents. The effects of substituents on the absorption spectra of spirohydantoins are interpreted by correlation of absorption frequencies with Hammett equation. The lipophilicities of the investigated molecules were estimated by calculation of their log P values. Some of the spirohydantoins synthesized in this work, exhibit the lipophilicities comparable to the standard medicine anticonvulsant drug Phenytoin. The results obtained in this investigation afford guidelines for the preparation of new derivatives of spirohydantoin as potential anticonvulsant agents and for better understanding the structure-activity relationship.",
publisher = "Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study",
pages = "98-88",
volume = "1127",
doi = "10.1016/j.molstruc.2016.07.069"
}

Lazić, A. M., Božić, B. Ð., Vitnik, V. D., Vitnik, Ž. J., Rogan, J. R., Radovanović, L. D., Valentić, N. V.,& Ušćumlić, G. S.. (2017). Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study. in Journal of Molecular Structure
Elsevier B.V.., 1127, 88-98.
https://doi.org/10.1016/j.molstruc.2016.07.069

Lazić AM, Božić BÐ, Vitnik VD, Vitnik ŽJ, Rogan JR, Radovanović LD, Valentić NV, Ušćumlić GS. Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study. in Journal of Molecular Structure. 2017;1127:88-98.
doi:10.1016/j.molstruc.2016.07.069 .

Lazić, Anita M., Božić, Bojan Ð., Vitnik, Vesna D., Vitnik, Željko J., Rogan, Jelena R., Radovanović, Lidija D., Valentić, Nataša V., Ušćumlić, Gordana S., "Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study" in Journal of Molecular Structure, 1127 (2017):88-98,
https://doi.org/10.1016/j.molstruc.2016.07.069 . .

TY  - JOUR
AU  - Antanasijević, Davor
AU  - Antanasijević, Jelena
AU  - Trišović, Nemanja
AU  - Ušćumlić, Gordana
AU  - Pocajt, Viktor
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3614
AB  - Succinimides, which contain a pharmacophore responsible for anticonvulsant activity, are frequently used antiepileptic drugs and the synthesis of their new derivatives with improved efficacy and tolerability presents an important task. Nowadays, multitarget/tasking methodologies focused on quantitative-structure activity relationships (mt-QSAR/mtk-QSAR) have an important role in the rational design of drugs since they enable simultaneous prediction of several standard measures of biological activities at diverse experimental conditions and against different biological targets. Relating to this very topic, the mt-QSAR/mtk-QSAR methodology can give only binary classification models, and as such, in this study a regression mtk-QSAR (rmtk-QSAR) model based on a novel modular neural network (MNN) has been proposed. The MNN uses standard classification mtk-QSAR models as input modules, while the regression is performed by the output module. The rmtk-QSAR model has been successfully developed for the simultaneous prediction of anticonvulsant activity and neurotoxicity of succinimides, with a satisfactory accuracy in testing (R-2 = 0.87). Thus, the proposed mtk-QSAR regression method can be regarded as a viable alternative to the standard QSAR methodology.
PB  - Amer Chemical Soc, Washington
T2  - Molecular Pharmaceutics
T1  - From Classification to Regression Multitasking QSAR Modeling Using a Novel Modular Neural Network: Simultaneous Prediction of Anticonvulsant Activity and Neurotoxicity of Succinimides
EP  - 4484
IS  - 12
SP  - 4476
VL  - 14
DO  - 10.1021/acs.molpharmaceut.7b00582
ER  - 

@article{
author = "Antanasijević, Davor and Antanasijević, Jelena and Trišović, Nemanja and Ušćumlić, Gordana and Pocajt, Viktor",
year = "2017",
abstract = "Succinimides, which contain a pharmacophore responsible for anticonvulsant activity, are frequently used antiepileptic drugs and the synthesis of their new derivatives with improved efficacy and tolerability presents an important task. Nowadays, multitarget/tasking methodologies focused on quantitative-structure activity relationships (mt-QSAR/mtk-QSAR) have an important role in the rational design of drugs since they enable simultaneous prediction of several standard measures of biological activities at diverse experimental conditions and against different biological targets. Relating to this very topic, the mt-QSAR/mtk-QSAR methodology can give only binary classification models, and as such, in this study a regression mtk-QSAR (rmtk-QSAR) model based on a novel modular neural network (MNN) has been proposed. The MNN uses standard classification mtk-QSAR models as input modules, while the regression is performed by the output module. The rmtk-QSAR model has been successfully developed for the simultaneous prediction of anticonvulsant activity and neurotoxicity of succinimides, with a satisfactory accuracy in testing (R-2 = 0.87). Thus, the proposed mtk-QSAR regression method can be regarded as a viable alternative to the standard QSAR methodology.",
publisher = "Amer Chemical Soc, Washington",
journal = "Molecular Pharmaceutics",
title = "From Classification to Regression Multitasking QSAR Modeling Using a Novel Modular Neural Network: Simultaneous Prediction of Anticonvulsant Activity and Neurotoxicity of Succinimides",
pages = "4484-4476",
number = "12",
volume = "14",
doi = "10.1021/acs.molpharmaceut.7b00582"
}

Antanasijević, D., Antanasijević, J., Trišović, N., Ušćumlić, G.,& Pocajt, V.. (2017). From Classification to Regression Multitasking QSAR Modeling Using a Novel Modular Neural Network: Simultaneous Prediction of Anticonvulsant Activity and Neurotoxicity of Succinimides. in Molecular Pharmaceutics
Amer Chemical Soc, Washington., 14(12), 4476-4484.
https://doi.org/10.1021/acs.molpharmaceut.7b00582

Antanasijević D, Antanasijević J, Trišović N, Ušćumlić G, Pocajt V. From Classification to Regression Multitasking QSAR Modeling Using a Novel Modular Neural Network: Simultaneous Prediction of Anticonvulsant Activity and Neurotoxicity of Succinimides. in Molecular Pharmaceutics. 2017;14(12):4476-4484.
doi:10.1021/acs.molpharmaceut.7b00582 .

Antanasijević, Davor, Antanasijević, Jelena, Trišović, Nemanja, Ušćumlić, Gordana, Pocajt, Viktor, "From Classification to Regression Multitasking QSAR Modeling Using a Novel Modular Neural Network: Simultaneous Prediction of Anticonvulsant Activity and Neurotoxicity of Succinimides" in Molecular Pharmaceutics, 14, no. 12 (2017):4476-4484,
https://doi.org/10.1021/acs.molpharmaceut.7b00582 . .

TY  - JOUR
AU  - Božić, Bojan
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Rančić, Milica
AU  - Trišović, Nemanja
AU  - Božić, Biljana
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3607
AB  - A series of six novel 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acids and six corresponding methyl esters were synthesized. All compounds were characterized by melting points, elemental analysis, FT-IR, H-1 and C-13 NMR spectroscopy. Crystal structure of methyl-2-(5-(4-methoxybenzylidene)-2,4-dioxotetrahydrothiazole-3-yl) propionate was confirmed by X-ray analysis. The antiproliferative activity of all synthesized compounds against human colon cancer, breast cancer and myelogenous leukemia cell lines, i.e. HCT-116, MDA-231 and K562, respectively, was evaluated. The results indicate that antiproliferative activity of the synthesized esters is better than the activity of the corresponding acids. All synthesized compounds showed significant antiproliferative effects against HCT116 cells in all tested concentrations (0.01-100 lM). Moreover, in vitro antimicrobial activity against a wide range of tested microorganisms was examined.
PB  - Elsevier Science Bv, Amsterdam
T2  - Arabian Journal of Chemistry
T1  - Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives
EP  - S2643
SP  - S2637
VL  - 10
DO  - 10.1016/j.arabjc.2013.10.002
ER  - 

@article{
author = "Božić, Bojan and Rogan, Jelena and Poleti, Dejan and Rančić, Milica and Trišović, Nemanja and Božić, Biljana and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of six novel 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acids and six corresponding methyl esters were synthesized. All compounds were characterized by melting points, elemental analysis, FT-IR, H-1 and C-13 NMR spectroscopy. Crystal structure of methyl-2-(5-(4-methoxybenzylidene)-2,4-dioxotetrahydrothiazole-3-yl) propionate was confirmed by X-ray analysis. The antiproliferative activity of all synthesized compounds against human colon cancer, breast cancer and myelogenous leukemia cell lines, i.e. HCT-116, MDA-231 and K562, respectively, was evaluated. The results indicate that antiproliferative activity of the synthesized esters is better than the activity of the corresponding acids. All synthesized compounds showed significant antiproliferative effects against HCT116 cells in all tested concentrations (0.01-100 lM). Moreover, in vitro antimicrobial activity against a wide range of tested microorganisms was examined.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Arabian Journal of Chemistry",
title = "Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives",
pages = "S2643-S2637",
volume = "10",
doi = "10.1016/j.arabjc.2013.10.002"
}

Božić, B., Rogan, J., Poleti, D., Rančić, M., Trišović, N., Božić, B.,& Ušćumlić, G.. (2017). Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives. in Arabian Journal of Chemistry
Elsevier Science Bv, Amsterdam., 10, S2637-S2643.
https://doi.org/10.1016/j.arabjc.2013.10.002

Božić B, Rogan J, Poleti D, Rančić M, Trišović N, Božić B, Ušćumlić G. Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives. in Arabian Journal of Chemistry. 2017;10:S2637-S2643.
doi:10.1016/j.arabjc.2013.10.002 .

Božić, Bojan, Rogan, Jelena, Poleti, Dejan, Rančić, Milica, Trišović, Nemanja, Božić, Biljana, Ušćumlić, Gordana, "Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives" in Arabian Journal of Chemistry, 10 (2017):S2637-S2643,
https://doi.org/10.1016/j.arabjc.2013.10.002 . .

TY  - JOUR
AU  - Banjac, Nebojša
AU  - Božić, Bojan
AU  - Lađarević, Jelena
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Valentić, Nataša
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3663
AB  - A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides
EP  - 282
SP  - 271
VL  - 1129
DO  - 10.1016/j.molstruc.2016.09.086
ER  - 

@article{
author = "Banjac, Nebojša and Božić, Bojan and Lađarević, Jelena and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides",
pages = "282-271",
volume = "1129",
doi = "10.1016/j.molstruc.2016.09.086"
}

Banjac, N., Božić, B., Lađarević, J., Vitnik, V., Vitnik, Ž., Valentić, N.,& Ušćumlić, G.. (2017). Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 1129, 271-282.
https://doi.org/10.1016/j.molstruc.2016.09.086

Banjac N, Božić B, Lađarević J, Vitnik V, Vitnik Ž, Valentić N, Ušćumlić G. Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure. 2017;1129:271-282.
doi:10.1016/j.molstruc.2016.09.086 .

Banjac, Nebojša, Božić, Bojan, Lađarević, Jelena, Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša, Ušćumlić, Gordana, "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides" in Journal of Molecular Structure, 1129 (2017):271-282,
https://doi.org/10.1016/j.molstruc.2016.09.086 . .

TY  - JOUR
AU  - Lazić, Anita
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3698
AB  - A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.
PB  - Royal Society of Chemistry
T2  - CrystEngComm
T1  - Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety
EP  - 483
IS  - 3
SP  - 469
VL  - 19
DO  - 10.1039/c6ce02210c
ER  - 

@article{
author = "Lazić, Anita and Trišović, Nemanja and Radovanović, Lidija and Rogan, Jelena and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.",
publisher = "Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety",
pages = "483-469",
number = "3",
volume = "19",
doi = "10.1039/c6ce02210c"
}

Lazić, A., Trišović, N., Radovanović, L., Rogan, J., Poleti, D., Vitnik, Ž., Vitnik, V.,& Ušćumlić, G.. (2017). Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in CrystEngComm
Royal Society of Chemistry., 19(3), 469-483.
https://doi.org/10.1039/c6ce02210c

Lazić A, Trišović N, Radovanović L, Rogan J, Poleti D, Vitnik Ž, Vitnik V, Ušćumlić G. Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in CrystEngComm. 2017;19(3):469-483.
doi:10.1039/c6ce02210c .

Lazić, Anita, Trišović, Nemanja, Radovanović, Lidija, Rogan, Jelena, Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Ušćumlić, Gordana, "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety" in CrystEngComm, 19, no. 3 (2017):469-483,
https://doi.org/10.1039/c6ce02210c . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Božić, Bojan
AU  - Valentić, Nataša
AU  - Dilber, Sanda P.
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3746
AB  - In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating -OCH3 and electron-withdrawing -NO2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes.
PB  - Wiley, Hoboken
T2  - Coloration Technology
T1  - Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes
EP  - 233
IS  - 3
SP  - 223
VL  - 133
DO  - 10.1111/cote.12271
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Božić, Bojan and Valentić, Nataša and Dilber, Sanda P. and Mijin, Dušan and Ušćumlić, Gordana",
year = "2017",
abstract = "In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating -OCH3 and electron-withdrawing -NO2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes.",
publisher = "Wiley, Hoboken",
journal = "Coloration Technology",
title = "Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes",
pages = "233-223",
number = "3",
volume = "133",
doi = "10.1111/cote.12271"
}

Vitnik, V., Vitnik, Ž., Božić, B., Valentić, N., Dilber, S. P., Mijin, D.,& Ušćumlić, G.. (2017). Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes. in Coloration Technology
Wiley, Hoboken., 133(3), 223-233.
https://doi.org/10.1111/cote.12271

Vitnik V, Vitnik Ž, Božić B, Valentić N, Dilber SP, Mijin D, Ušćumlić G. Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes. in Coloration Technology. 2017;133(3):223-233.
doi:10.1111/cote.12271 .

Vitnik, Vesna, Vitnik, Željko, Božić, Bojan, Valentić, Nataša, Dilber, Sanda P., Mijin, Dušan, Ušćumlić, Gordana, "Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes" in Coloration Technology, 133, no. 3 (2017):223-233,
https://doi.org/10.1111/cote.12271 . .

TY  - JOUR
AU  - Milošević, Nataša P.
AU  - Kojić, Vesna
AU  - Curcić, Jelena
AU  - Jakimov, Dimitar
AU  - Milić, Nataša
AU  - Banjac, Nebojša
AU  - Ušćumlić, Gordana
AU  - Kaliszan, Roman
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5819
AB  - Design of a new drug entity is usually preceded by analysis of quantitative structure activity (properties) relationships, QSA(P)R. Six newly synthesized succinimide derivatives have been determined for (i) in silico physico-chemical descriptors, pharmacokinetic and toxicity predictors, (ii) in vitro biological activity on four different carcinoma cell lines and on normal fetal lung cells and (iii) lipophilicity on liquid chromatography. All compounds observed were predicted for good permeability and solubility, good oral absorption rate and moderate volume of distribution as well as for modest blood brain permeation, followed by acceptable observed toxicity. In silico determined lipophilicity, permeability through jejunum and aqueous solubility were correlated with experimentally obtained lipophilic constants (by use of high pressure liquid chromatography) and linear correlations were obtained. Absorption rate and volume of distribution were predicted by chromatographic lipophilicity measurements while permeation through blood bran barrier was predicted dominantly by molecular size defined with molecular weight. Five compounds have demonstrated antiproliferative activity toward cervix carcinoma HeLa cell lines; three were cytotoxic against breast carcinoma MCF-7 cells, while one inhibited proliferation of colon carcinoma HT 29 cell lines. Only one compound was cytotoxic toward normal cell lines, while other compounds were proven as safe. Antiproliferative potential against HeLa cells was described as exponential function of lipophilicity. Based on obtained results, lead compounds were selected.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Evaluation of in silico pharmacokinetic properties and in vitro cytotoxic activity of selected newly synthesized N-succinimide derivatives
EP  - 257
SP  - 252
VL  - 137
DO  - 10.1016/j.jpba.2017.01.042
ER  - 

@article{
author = "Milošević, Nataša P. and Kojić, Vesna and Curcić, Jelena and Jakimov, Dimitar and Milić, Nataša and Banjac, Nebojša and Ušćumlić, Gordana and Kaliszan, Roman",
year = "2017",
abstract = "Design of a new drug entity is usually preceded by analysis of quantitative structure activity (properties) relationships, QSA(P)R. Six newly synthesized succinimide derivatives have been determined for (i) in silico physico-chemical descriptors, pharmacokinetic and toxicity predictors, (ii) in vitro biological activity on four different carcinoma cell lines and on normal fetal lung cells and (iii) lipophilicity on liquid chromatography. All compounds observed were predicted for good permeability and solubility, good oral absorption rate and moderate volume of distribution as well as for modest blood brain permeation, followed by acceptable observed toxicity. In silico determined lipophilicity, permeability through jejunum and aqueous solubility were correlated with experimentally obtained lipophilic constants (by use of high pressure liquid chromatography) and linear correlations were obtained. Absorption rate and volume of distribution were predicted by chromatographic lipophilicity measurements while permeation through blood bran barrier was predicted dominantly by molecular size defined with molecular weight. Five compounds have demonstrated antiproliferative activity toward cervix carcinoma HeLa cell lines; three were cytotoxic against breast carcinoma MCF-7 cells, while one inhibited proliferation of colon carcinoma HT 29 cell lines. Only one compound was cytotoxic toward normal cell lines, while other compounds were proven as safe. Antiproliferative potential against HeLa cells was described as exponential function of lipophilicity. Based on obtained results, lead compounds were selected.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Evaluation of in silico pharmacokinetic properties and in vitro cytotoxic activity of selected newly synthesized N-succinimide derivatives",
pages = "257-252",
volume = "137",
doi = "10.1016/j.jpba.2017.01.042"
}

Milošević, N. P., Kojić, V., Curcić, J., Jakimov, D., Milić, N., Banjac, N., Ušćumlić, G.,& Kaliszan, R.. (2017). Evaluation of in silico pharmacokinetic properties and in vitro cytotoxic activity of selected newly synthesized N-succinimide derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam., 137, 252-257.
https://doi.org/10.1016/j.jpba.2017.01.042

Milošević NP, Kojić V, Curcić J, Jakimov D, Milić N, Banjac N, Ušćumlić G, Kaliszan R. Evaluation of in silico pharmacokinetic properties and in vitro cytotoxic activity of selected newly synthesized N-succinimide derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2017;137:252-257.
doi:10.1016/j.jpba.2017.01.042 .

Milošević, Nataša P., Kojić, Vesna, Curcić, Jelena, Jakimov, Dimitar, Milić, Nataša, Banjac, Nebojša, Ušćumlić, Gordana, Kaliszan, Roman, "Evaluation of in silico pharmacokinetic properties and in vitro cytotoxic activity of selected newly synthesized N-succinimide derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 137 (2017):252-257,
https://doi.org/10.1016/j.jpba.2017.01.042 . .

TY  - CONF
AU  - Lazić, Anita
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Ušćumlić, Gordana
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6697
AB  - Analiza strukturnih svojstava novih jedinjenja koja sadrže čvrsto jezgro i višestruke donorske i akceptorske atome može da doprinese boljem razumevanju uzajamnog dejstva nekovalentnih interakcija u izgradnji mogućih supramolekulskih
arhitektura. U tom cilju sintetisana je serija novih derivata ciklopentan-5-spirohidantoina i određena je njihova kristalna struktura. U ovom radu opisana je i
diskutovana kristalna struktura (3-[(4-bromofenil)metil]-1,3-diazaspiro[4.4]nonan-2,4-diona (slike 1 i 2). Jedinjenje kristališe u centrosimetričnoj, monokliničnoj prostornoj grupi P21/n sa jednim molekulom u asimetričnoj jedinici. Detaljna analiza kristalnog pakovanja ukazala je na postojanje uobičajenih
N–H···O vodoničnih veza, kao i na pojavu C–H···O, C–H···π i C–H···Br interakcija.
Takođe, nađeni su i kratki kontakti tipa C–Br···O=C. Doprinosi ovih interakcija
u izgradnji kristalnog pakovanja kvantifikovani su na osnovu izračunavanja metodom Coulomb–London–Pauli (CLP) [1]. U sprezi sa pregledom kristalnih struktura
derivata hidantoina u Kembričkoj bazi kristalnih struktura, razmatranje energije
interakcija različitih parova molekula omogućiće utvrđivanje zavisnosti između
njihove molekulske i kristalne strukture.
AB  - The analysis of structural features of new compounds comprising a rigid core with multiple donor and acceptor atoms can enhance our understanding of the interplay between
noncovalent interactions in building possible supramolecular assemblies. In this respect,
a series of new cyclopentane-5-spirohydantoin derivatives has been synthesized and their
crystal structures have been investigated (Figs. 1 and 2). Herein, the crystal structure of 3-
[(4-bromophenyl)methyl]-1,3-diazaspiro[4.4]nonane-2,4-dione is described and discussed. The compound crystallizes in the monoclinic, centrosymmetric space group P21/n
with one molecule in the asymmetric unit. A detailed analysis of the crystal packing revealed the presence of usual N–H···O hydrogen bonds along with C–H···O, C–H···π and
C–H···Br interactions. Furthermore, a short C–Br···O=C contact also contributed to the
crystal packing. The stabilizing–destabilizing role of these interactions in terms of favorable energetic was quantified using the Coulomb–London–Pauli (CLP) method [1].
Supported with a survey of crystal structures containing the hydantoin moiety in the
Cambridge Structural Database, the decomposition of the interaction energies obtained for
different molecular pairs will provide a base for the evaluation of the relationships between
molecular and crystal structure of hydantoin derivatives.
PB  - Beograd : Srpsko kristalografsko društvo
C3  - Izvodi radova / XXIII konferencija Srpskog kristalografskog društva, Andrevlje, 9-11. jun 2016
T1  - STRUKTURNA I CLP ANALIZA 3-[(4-BROMOFENIL)METIL]-1,3-DIAZASPIRO[4.4]NONAN-2,4-DIONA
T1  - STRUCTURAL AND CLP ANALYSIS OF 3-[(4-BROMOPHENYL)METHYL]- 1,3-DIAZASPIRO[4.4]NONANE-2,4-DIONE
EP  - 87
SP  - 86
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6697
ER  - 

@conference{
author = "Lazić, Anita and Trišović, Nemanja and Radovanović, Lidija and Vitnik, Željko and Vitnik, Vesna and Rogan, Jelena and Poleti, Dejan and Ušćumlić, Gordana",
year = "2016",
abstract = "Analiza strukturnih svojstava novih jedinjenja koja sadrže čvrsto jezgro i višestruke donorske i akceptorske atome može da doprinese boljem razumevanju uzajamnog dejstva nekovalentnih interakcija u izgradnji mogućih supramolekulskih
arhitektura. U tom cilju sintetisana je serija novih derivata ciklopentan-5-spirohidantoina i određena je njihova kristalna struktura. U ovom radu opisana je i
diskutovana kristalna struktura (3-[(4-bromofenil)metil]-1,3-diazaspiro[4.4]nonan-2,4-diona (slike 1 i 2). Jedinjenje kristališe u centrosimetričnoj, monokliničnoj prostornoj grupi P21/n sa jednim molekulom u asimetričnoj jedinici. Detaljna analiza kristalnog pakovanja ukazala je na postojanje uobičajenih
N–H···O vodoničnih veza, kao i na pojavu C–H···O, C–H···π i C–H···Br interakcija.
Takođe, nađeni su i kratki kontakti tipa C–Br···O=C. Doprinosi ovih interakcija
u izgradnji kristalnog pakovanja kvantifikovani su na osnovu izračunavanja metodom Coulomb–London–Pauli (CLP) [1]. U sprezi sa pregledom kristalnih struktura
derivata hidantoina u Kembričkoj bazi kristalnih struktura, razmatranje energije
interakcija različitih parova molekula omogućiće utvrđivanje zavisnosti između
njihove molekulske i kristalne strukture., The analysis of structural features of new compounds comprising a rigid core with multiple donor and acceptor atoms can enhance our understanding of the interplay between
noncovalent interactions in building possible supramolecular assemblies. In this respect,
a series of new cyclopentane-5-spirohydantoin derivatives has been synthesized and their
crystal structures have been investigated (Figs. 1 and 2). Herein, the crystal structure of 3-
[(4-bromophenyl)methyl]-1,3-diazaspiro[4.4]nonane-2,4-dione is described and discussed. The compound crystallizes in the monoclinic, centrosymmetric space group P21/n
with one molecule in the asymmetric unit. A detailed analysis of the crystal packing revealed the presence of usual N–H···O hydrogen bonds along with C–H···O, C–H···π and
C–H···Br interactions. Furthermore, a short C–Br···O=C contact also contributed to the
crystal packing. The stabilizing–destabilizing role of these interactions in terms of favorable energetic was quantified using the Coulomb–London–Pauli (CLP) method [1].
Supported with a survey of crystal structures containing the hydantoin moiety in the
Cambridge Structural Database, the decomposition of the interaction energies obtained for
different molecular pairs will provide a base for the evaluation of the relationships between
molecular and crystal structure of hydantoin derivatives.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXIII konferencija Srpskog kristalografskog društva, Andrevlje, 9-11. jun 2016",
title = "STRUKTURNA I CLP ANALIZA 3-[(4-BROMOFENIL)METIL]-1,3-DIAZASPIRO[4.4]NONAN-2,4-DIONA, STRUCTURAL AND CLP ANALYSIS OF 3-[(4-BROMOPHENYL)METHYL]- 1,3-DIAZASPIRO[4.4]NONANE-2,4-DIONE",
pages = "87-86",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6697"
}

Lazić, A., Trišović, N., Radovanović, L., Vitnik, Ž., Vitnik, V., Rogan, J., Poleti, D.,& Ušćumlić, G.. (2016). STRUKTURNA I CLP ANALIZA 3-[(4-BROMOFENIL)METIL]-1,3-DIAZASPIRO[4.4]NONAN-2,4-DIONA. in Izvodi radova / XXIII konferencija Srpskog kristalografskog društva, Andrevlje, 9-11. jun 2016
Beograd : Srpsko kristalografsko društvo., 86-87.
https://hdl.handle.net/21.15107/rcub_technorep_6697

Lazić A, Trišović N, Radovanović L, Vitnik Ž, Vitnik V, Rogan J, Poleti D, Ušćumlić G. STRUKTURNA I CLP ANALIZA 3-[(4-BROMOFENIL)METIL]-1,3-DIAZASPIRO[4.4]NONAN-2,4-DIONA. in Izvodi radova / XXIII konferencija Srpskog kristalografskog društva, Andrevlje, 9-11. jun 2016. 2016;:86-87.
https://hdl.handle.net/21.15107/rcub_technorep_6697 .

Lazić, Anita, Trišović, Nemanja, Radovanović, Lidija, Vitnik, Željko, Vitnik, Vesna, Rogan, Jelena, Poleti, Dejan, Ušćumlić, Gordana, "STRUKTURNA I CLP ANALIZA 3-[(4-BROMOFENIL)METIL]-1,3-DIAZASPIRO[4.4]NONAN-2,4-DIONA" in Izvodi radova / XXIII konferencija Srpskog kristalografskog društva, Andrevlje, 9-11. jun 2016 (2016):86-87,
https://hdl.handle.net/21.15107/rcub_technorep_6697 .

TY  - CONF
AU  - Lazić, Anita M.
AU  - Božić, Bojan Đ.
AU  - Božić, Biljana Đ.
AU  - Ušćumlić, Gordana S.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6763
AB  - Spirohidantoini pripadaju grupi jedinjenja koja ispoljavaju širok spektar biološke aktivnosti. Do
sada su derivati spirohidantoina identifikovani kao antikonvulzivi, antiaritmici, antidijabetici i
antitumorni agensi. U cilju ispitivanja biološke aktivnosti, testirana je citotoksičnost novih serija
jedinjenja: 3-(4-supstituisanih benzil)-1,3-diazaspiro[4.5]dekan-2,4-diona, 3-(2-(4-supstituisanih
fenil)-2-oksoetil)-1,3-diazaspiro-[4.5]-dekan-2,4-diona, 3-(4-supstituisanih benzil)-1,3-diazaspiro[4.6]undekan-2,4-diona i 3-(2-(4-supstituisanih fenil)-2-oksoetil)-1,3-diazaspiro[4.6]undekan-
-2,4-diona. Citotoksična aktivnost određena je MTT testom prema ćelijskim linijama humane
mijeloidne leukemije (K562), raka debelog creva (HCT-116) i raka dojke (MDA-MB-231). Testirana
jedinjenja pokazala su značajnu citotoksičnost prema svim ćelijskim linijama, a naročito su se
istakli derivati koji u okviru svoje strukture sadrže halogene kao supstituente. Uticaj sternih i
elektronskih svojstava supstituenata na aktivnost proučavanih jedinjenja, analiziran je primenom
QSAR modela.
AB  - Spiroydantoins belong to a group of compounds exhibiting a wide range of biological activities. Until now, the spirohydantoin derivatives are identified as anticonvulsants, antiarrhythmic drugs, antidiabetic agents and antitumor agents. In order to investigate the biological activity was tested on the cytotoxicity of the new series of compounds: 3-(4-substituted benzyl)-1,3-diazaspiro[4.5]decane-2,4-dione, 3-(2-(4-substituted phenyl)-2-oxoethyl)-1,3-diazaspiro[4.5]decane2,4-dione, 3-(4-substituted benzyl)-1,3--diazaspiro-[4.6]undecane-2,4-dione and 3-(2-(4-substituted phenyl)-2-oxoethyl)-1,3-diazaspiro[4.6]-undecane-2,4-dione. Cytotoxic activity was assessed by MTT assay cell lines of human myeloid leukemia (K562), colon (HCT-116) and breast cancer cells (MDA-MB-231). The test compounds showed a significant cytotoxicity to all cell lines, and in particular the derivatives containig within its structure halogens as substituents. The effect of steric and electronic properties of the substituents on activity of studed compounds, was analyzed by QSAR models.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016
T1  - Dizajn, sinteza i antiproliferativna aktivnost novih cikloalkanspiro-5-hidantoinskih derivata: Veza između strukture i aktivnosti
T1  - Design, synthesis and antiproliferative evaluation of novel cycloalkane-spiro-5-hydantoin derivatives: A structure-activity relationship study
SP  - 56
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6763
ER  - 

@conference{
author = "Lazić, Anita M. and Božić, Bojan Đ. and Božić, Biljana Đ. and Ušćumlić, Gordana S.",
year = "2016",
abstract = "Spirohidantoini pripadaju grupi jedinjenja koja ispoljavaju širok spektar biološke aktivnosti. Do
sada su derivati spirohidantoina identifikovani kao antikonvulzivi, antiaritmici, antidijabetici i
antitumorni agensi. U cilju ispitivanja biološke aktivnosti, testirana je citotoksičnost novih serija
jedinjenja: 3-(4-supstituisanih benzil)-1,3-diazaspiro[4.5]dekan-2,4-diona, 3-(2-(4-supstituisanih
fenil)-2-oksoetil)-1,3-diazaspiro-[4.5]-dekan-2,4-diona, 3-(4-supstituisanih benzil)-1,3-diazaspiro[4.6]undekan-2,4-diona i 3-(2-(4-supstituisanih fenil)-2-oksoetil)-1,3-diazaspiro[4.6]undekan-
-2,4-diona. Citotoksična aktivnost određena je MTT testom prema ćelijskim linijama humane
mijeloidne leukemije (K562), raka debelog creva (HCT-116) i raka dojke (MDA-MB-231). Testirana
jedinjenja pokazala su značajnu citotoksičnost prema svim ćelijskim linijama, a naročito su se
istakli derivati koji u okviru svoje strukture sadrže halogene kao supstituente. Uticaj sternih i
elektronskih svojstava supstituenata na aktivnost proučavanih jedinjenja, analiziran je primenom
QSAR modela., Spiroydantoins belong to a group of compounds exhibiting a wide range of biological activities. Until now, the spirohydantoin derivatives are identified as anticonvulsants, antiarrhythmic drugs, antidiabetic agents and antitumor agents. In order to investigate the biological activity was tested on the cytotoxicity of the new series of compounds: 3-(4-substituted benzyl)-1,3-diazaspiro[4.5]decane-2,4-dione, 3-(2-(4-substituted phenyl)-2-oxoethyl)-1,3-diazaspiro[4.5]decane2,4-dione, 3-(4-substituted benzyl)-1,3--diazaspiro-[4.6]undecane-2,4-dione and 3-(2-(4-substituted phenyl)-2-oxoethyl)-1,3-diazaspiro[4.6]-undecane-2,4-dione. Cytotoxic activity was assessed by MTT assay cell lines of human myeloid leukemia (K562), colon (HCT-116) and breast cancer cells (MDA-MB-231). The test compounds showed a significant cytotoxicity to all cell lines, and in particular the derivatives containig within its structure halogens as substituents. The effect of steric and electronic properties of the substituents on activity of studed compounds, was analyzed by QSAR models.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016",
title = "Dizajn, sinteza i antiproliferativna aktivnost novih cikloalkanspiro-5-hidantoinskih derivata: Veza između strukture i aktivnosti, Design, synthesis and antiproliferative evaluation of novel cycloalkane-spiro-5-hydantoin derivatives: A structure-activity relationship study",
pages = "56",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6763"
}

Lazić, A. M., Božić, B. Đ., Božić, B. Đ.,& Ušćumlić, G. S.. (2016). Dizajn, sinteza i antiproliferativna aktivnost novih cikloalkanspiro-5-hidantoinskih derivata: Veza između strukture i aktivnosti. in Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016
Beograd : Srpsko hemijsko društvo., 56.
https://hdl.handle.net/21.15107/rcub_technorep_6763

Lazić AM, Božić BĐ, Božić BĐ, Ušćumlić GS. Dizajn, sinteza i antiproliferativna aktivnost novih cikloalkanspiro-5-hidantoinskih derivata: Veza između strukture i aktivnosti. in Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016. 2016;:56.
https://hdl.handle.net/21.15107/rcub_technorep_6763 .

Lazić, Anita M., Božić, Bojan Đ., Božić, Biljana Đ., Ušćumlić, Gordana S., "Dizajn, sinteza i antiproliferativna aktivnost novih cikloalkanspiro-5-hidantoinskih derivata: Veza između strukture i aktivnosti" in Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016 (2016):56,
https://hdl.handle.net/21.15107/rcub_technorep_6763 .

TY  - CONF
AU  - Mandić, Željko
AU  - Lazić, Anita M.
AU  - Božić, Bojan Đ.
AU  - Ušćumlić, Gordana S.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6762
AB  - Derivati tetrantoina (7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona) (Slika ) su jedinjenja širokog
spektra biološke aktivnosti. Mnogi od njih su poznata antikonvulzivna, antivirusna i antikancerogena jedinjenja, a uspešno se koriste i u lečenju dijabetesa. U okviru ovog rada, sintetizovan
je tetrantoin i njegovi derivati koji u položaju 3 hidantoinskog prstena sadrže supstituisanu benzil
grupu (supstituent X: H, CH3, OCH3, Cl, Br, CN). Struktura navedenih jedinjenja potvrđena je
temperaturama topljenja, 1 H i 13 C NMR, Ft-IR i UV spektroskopskim metodama. Na osnovu
strukturnih i lipofilnih karakteristika diskutovana je potencijalna biološka aktivnost sintetizovanih jedinjenja.
AB  - Derivatives of tetrantoin (7,8-benzo-1,3-diazaspiro[4.5]decane-2,4-dione) (Figure) are the compounds of a wide range of biological activities. Many of them are known anticonvulsant, anticancer and antiviral compounds, and are successfully used in the treatment of diabetes. In this work, was synthesized tetrantoin and its derivatives which in the 3-position of the hydantoin ring containing a substituted benzyl group (the substituent X: H, CH3, OCH3, Cl, Br, CN). The structure of these compounds was confirmed by melting point, 1H and 13C NMR, FT-IR and UV spectroscopic methods. Based on structural lipophilic characteristics is discussed the potential biological activity of the synthesized compounds.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016
T1  - Sinteza, struktura i svojstva 7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona i njegovih derivata
T1  - Synthesis, structure and properties of 7,8-benzo-1,3-diazaspiro[4.5]decane-2,4-dione and its derivatives
SP  - 55
UR  - https://hdl.handle.net/21.15107/rcub_technorep_6762
ER  - 

@conference{
author = "Mandić, Željko and Lazić, Anita M. and Božić, Bojan Đ. and Ušćumlić, Gordana S.",
year = "2016",
abstract = "Derivati tetrantoina (7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona) (Slika ) su jedinjenja širokog
spektra biološke aktivnosti. Mnogi od njih su poznata antikonvulzivna, antivirusna i antikancerogena jedinjenja, a uspešno se koriste i u lečenju dijabetesa. U okviru ovog rada, sintetizovan
je tetrantoin i njegovi derivati koji u položaju 3 hidantoinskog prstena sadrže supstituisanu benzil
grupu (supstituent X: H, CH3, OCH3, Cl, Br, CN). Struktura navedenih jedinjenja potvrđena je
temperaturama topljenja, 1 H i 13 C NMR, Ft-IR i UV spektroskopskim metodama. Na osnovu
strukturnih i lipofilnih karakteristika diskutovana je potencijalna biološka aktivnost sintetizovanih jedinjenja., Derivatives of tetrantoin (7,8-benzo-1,3-diazaspiro[4.5]decane-2,4-dione) (Figure) are the compounds of a wide range of biological activities. Many of them are known anticonvulsant, anticancer and antiviral compounds, and are successfully used in the treatment of diabetes. In this work, was synthesized tetrantoin and its derivatives which in the 3-position of the hydantoin ring containing a substituted benzyl group (the substituent X: H, CH3, OCH3, Cl, Br, CN). The structure of these compounds was confirmed by melting point, 1H and 13C NMR, FT-IR and UV spectroscopic methods. Based on structural lipophilic characteristics is discussed the potential biological activity of the synthesized compounds.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016",
title = "Sinteza, struktura i svojstva 7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona i njegovih derivata, Synthesis, structure and properties of 7,8-benzo-1,3-diazaspiro[4.5]decane-2,4-dione and its derivatives",
pages = "55",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6762"
}

Mandić, Ž., Lazić, A. M., Božić, B. Đ.,& Ušćumlić, G. S.. (2016). Sinteza, struktura i svojstva 7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona i njegovih derivata. in Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016
Beograd : Srpsko hemijsko društvo., 55.
https://hdl.handle.net/21.15107/rcub_technorep_6762

Mandić Ž, Lazić AM, Božić BĐ, Ušćumlić GS. Sinteza, struktura i svojstva 7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona i njegovih derivata. in Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016. 2016;:55.
https://hdl.handle.net/21.15107/rcub_technorep_6762 .

Mandić, Željko, Lazić, Anita M., Božić, Bojan Đ., Ušćumlić, Gordana S., "Sinteza, struktura i svojstva 7,8-benzo-1,3-diazaspiro[4.5]dekan-2,4-diona i njegovih derivata" in Kratki izvodi radova / Četvrta konferencija mladih hemičara Srbije, Beograd, 5. novembar 2016 (2016):55,
https://hdl.handle.net/21.15107/rcub_technorep_6762 .