TY  - JOUR
AU  - Hmuda, Sleem F.
AU  - Trišović, Nemanja
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Valentić, Nataša
AU  - Božić, Biljana
AU  - Ušćumlić, Gordana
PY  - 2014
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2862
AB  - Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations
EP  - 833
IS  - 5
SP  - 821
VL  - 145
DO  - 10.1007/s00706-013-1149-6
ER  - 

@article{
author = "Hmuda, Sleem F. and Trišović, Nemanja and Rogan, Jelena and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša and Božić, Biljana and Ušćumlić, Gordana",
year = "2014",
abstract = "Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations",
pages = "833-821",
number = "5",
volume = "145",
doi = "10.1007/s00706-013-1149-6"
}

Hmuda, S. F., Trišović, N., Rogan, J., Poleti, D., Vitnik, Ž., Vitnik, V., Valentić, N., Božić, B.,& Ušćumlić, G.. (2014). New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations. in Monatshefte Fur Chemie
Springer Wien, Wien., 145(5), 821-833.
https://doi.org/10.1007/s00706-013-1149-6

Hmuda SF, Trišović N, Rogan J, Poleti D, Vitnik Ž, Vitnik V, Valentić N, Božić B, Ušćumlić G. New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations. in Monatshefte Fur Chemie. 2014;145(5):821-833.
doi:10.1007/s00706-013-1149-6 .

Hmuda, Sleem F., Trišović, Nemanja, Rogan, Jelena, Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša, Božić, Biljana, Ušćumlić, Gordana, "New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations" in Monatshefte Fur Chemie, 145, no. 5 (2014):821-833,
https://doi.org/10.1007/s00706-013-1149-6 . .

TY  - JOUR
AU  - Hmuda, Sleem F.
AU  - Banjac, Nebojša
AU  - Trišović, Nemanja
AU  - Božić, Bojan
AU  - Valentić, Nataša
AU  - Ušćumlić, Gordana
PY  - 2013
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2364
AB  - To obtain insight into the interactions of potential anticonvulsant drugs with their surroundings, two series of 5-methyl-5-aryland 5-ethyl-5--arylhydantoins were synthesized and their absorption spectra were recorded in the region from 200 to 400 nm in a set of selected solvents. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen bonding interactions on the absorption maxima shifts were analyzed by means of the linear solvation energy relationship (LSER) concept of Kamlet and Taft. The ratio of the contributions of specific and non-specific solvent-solute interactions were correlated with the corresponding absorption, distribution, metabolism, and excretion (ADME) properties of the studied compounds. The correlation equations were combined with different physicochemical parameters to generate new equations, which demonstrate the reasonable relationships between the solvent-solute interactions and the structure-activity parameters.
AB  - Da bi se procenio način na koji potencijalni antikonvulzivni lekovi interaguju sa svojim okruženjem, dve serije 5-metil-5-(4-supstituisanih fenil)i 5-etil-5-(4supstituisanih fenil)hidantoina su sintetisane i njihovi apsorpcioni spektri su snimljeni u intervalu talasnih dužina od 200 do 400 nm u setu izabranih rastvarača. Efekti dipolarnosti/polarizabilnosti rastvarača i vodoničnog vezivanja između molekula rastvarača i rastvorene supstance na pomeranje apsorpcionih maksimuma analizirani su primenom metoda linearne korelacije energije solvatacije (LSER), odnosno Kamlet-Taftovom jednačinom. Odnos doprinosa specifičnih i nespecifičnih interakcija između molekula rastvarača i rastvorene supstance korelisani su sa odgovarajućim ADME svojstvima proučavanih jedinjenja. Korelacione jednačine su dalje kombinovane sa različitim fizičko-hemijskim parametrima pri čemu su dobijene nove jednačine koje na zadovoljavajući način opisuju odnose između interakcija između molekula rastvarača i rastvorene supstance i svojstava koja određuju njihovu aktivnost u organizmu.
PB  - Serbian Chemical Society, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study
T1  - Uticaj rastvarača na apsorpcione spektre potencijalno farmakološki aktivnih 5-alkil-5-arilhidantoinaproučavanje odnosa strukture i svojstava
EP  - 637
IS  - 5
SP  - 627
VL  - 78
UR  - https://hdl.handle.net/21.15107/rcub_technorep_2364
ER  - 

@article{
author = "Hmuda, Sleem F. and Banjac, Nebojša and Trišović, Nemanja and Božić, Bojan and Valentić, Nataša and Ušćumlić, Gordana",
year = "2013",
abstract = "To obtain insight into the interactions of potential anticonvulsant drugs with their surroundings, two series of 5-methyl-5-aryland 5-ethyl-5--arylhydantoins were synthesized and their absorption spectra were recorded in the region from 200 to 400 nm in a set of selected solvents. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen bonding interactions on the absorption maxima shifts were analyzed by means of the linear solvation energy relationship (LSER) concept of Kamlet and Taft. The ratio of the contributions of specific and non-specific solvent-solute interactions were correlated with the corresponding absorption, distribution, metabolism, and excretion (ADME) properties of the studied compounds. The correlation equations were combined with different physicochemical parameters to generate new equations, which demonstrate the reasonable relationships between the solvent-solute interactions and the structure-activity parameters., Da bi se procenio način na koji potencijalni antikonvulzivni lekovi interaguju sa svojim okruženjem, dve serije 5-metil-5-(4-supstituisanih fenil)i 5-etil-5-(4supstituisanih fenil)hidantoina su sintetisane i njihovi apsorpcioni spektri su snimljeni u intervalu talasnih dužina od 200 do 400 nm u setu izabranih rastvarača. Efekti dipolarnosti/polarizabilnosti rastvarača i vodoničnog vezivanja između molekula rastvarača i rastvorene supstance na pomeranje apsorpcionih maksimuma analizirani su primenom metoda linearne korelacije energije solvatacije (LSER), odnosno Kamlet-Taftovom jednačinom. Odnos doprinosa specifičnih i nespecifičnih interakcija između molekula rastvarača i rastvorene supstance korelisani su sa odgovarajućim ADME svojstvima proučavanih jedinjenja. Korelacione jednačine su dalje kombinovane sa različitim fizičko-hemijskim parametrima pri čemu su dobijene nove jednačine koje na zadovoljavajući način opisuju odnose između interakcija između molekula rastvarača i rastvorene supstance i svojstava koja određuju njihovu aktivnost u organizmu.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study, Uticaj rastvarača na apsorpcione spektre potencijalno farmakološki aktivnih 5-alkil-5-arilhidantoinaproučavanje odnosa strukture i svojstava",
pages = "637-627",
number = "5",
volume = "78",
url = "https://hdl.handle.net/21.15107/rcub_technorep_2364"
}

Hmuda, S. F., Banjac, N., Trišović, N., Božić, B., Valentić, N.,& Ušćumlić, G.. (2013). Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 78(5), 627-637.
https://hdl.handle.net/21.15107/rcub_technorep_2364

Hmuda SF, Banjac N, Trišović N, Božić B, Valentić N, Ušćumlić G. Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study. in Journal of the Serbian Chemical Society. 2013;78(5):627-637.
https://hdl.handle.net/21.15107/rcub_technorep_2364 .

Hmuda, Sleem F., Banjac, Nebojša, Trišović, Nemanja, Božić, Bojan, Valentić, Nataša, Ušćumlić, Gordana, "Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study" in Journal of the Serbian Chemical Society, 78, no. 5 (2013):627-637,
https://hdl.handle.net/21.15107/rcub_technorep_2364 .

TY  - JOUR
AU  - Hmuda, Sleem F.
AU  - Trišović, Nemanja
AU  - Valentić, Nataša
AU  - Ušćumlić, Gordana
PY  - 2011
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1930
AB  - Two series of 3-(4-substituted benzyl)-5-ethyl-5-phenyl- and 3-(4-substituted benzyl)-5,5-diphenylhydantoins were synthesized and their UV absorption spectra were recorded in the region 200-400 nm in selected solvents of different polarity. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions on the spectral shifts were analyzed by means of the linear solvation energy relationship (LSER) methodology of Kamlet and Taft. The quantitative relationships between hydrogen bonding interactions and the lipophilicity and blood-brain permeation of the studied compounds were discussed. Satisfactory linear dependences were obtained for moderate electron-donating and electron-withdrawing substituents at the benzyl moiety, while the strong electron-withdrawing substituent (NO2) significantly modifies the solvation characteristics of the molecule. The paper clearly demonstrates how the solvatochromic comparison method may be applied to estimate the contributions of various modes of solvation to the pharmaceutically relevant properties of these newly synthetized hydantoin derivatives.
PB  - Springer/Plenum Publishers, New York
T2  - Journal of Solution Chemistry
T1  - Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins
EP  - 319
IS  - 2
SP  - 307
VL  - 40
DO  - 10.1007/s10953-010-9641-7
ER  - 

@article{
author = "Hmuda, Sleem F. and Trišović, Nemanja and Valentić, Nataša and Ušćumlić, Gordana",
year = "2011",
abstract = "Two series of 3-(4-substituted benzyl)-5-ethyl-5-phenyl- and 3-(4-substituted benzyl)-5,5-diphenylhydantoins were synthesized and their UV absorption spectra were recorded in the region 200-400 nm in selected solvents of different polarity. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions on the spectral shifts were analyzed by means of the linear solvation energy relationship (LSER) methodology of Kamlet and Taft. The quantitative relationships between hydrogen bonding interactions and the lipophilicity and blood-brain permeation of the studied compounds were discussed. Satisfactory linear dependences were obtained for moderate electron-donating and electron-withdrawing substituents at the benzyl moiety, while the strong electron-withdrawing substituent (NO2) significantly modifies the solvation characteristics of the molecule. The paper clearly demonstrates how the solvatochromic comparison method may be applied to estimate the contributions of various modes of solvation to the pharmaceutically relevant properties of these newly synthetized hydantoin derivatives.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Journal of Solution Chemistry",
title = "Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins",
pages = "319-307",
number = "2",
volume = "40",
doi = "10.1007/s10953-010-9641-7"
}

Hmuda, S. F., Trišović, N., Valentić, N.,& Ušćumlić, G.. (2011). Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins. in Journal of Solution Chemistry
Springer/Plenum Publishers, New York., 40(2), 307-319.
https://doi.org/10.1007/s10953-010-9641-7

Hmuda SF, Trišović N, Valentić N, Ušćumlić G. Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins. in Journal of Solution Chemistry. 2011;40(2):307-319.
doi:10.1007/s10953-010-9641-7 .

Hmuda, Sleem F., Trišović, Nemanja, Valentić, Nataša, Ušćumlić, Gordana, "Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins" in Journal of Solution Chemistry, 40, no. 2 (2011):307-319,
https://doi.org/10.1007/s10953-010-9641-7 . .