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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

Authorized Users Only
2017
Authors
Lazić, Anita
Božić, Bojan
Vitnik, Vesna
Vitnik, Željko
Rogan, Jelena
Radovanović, Lidija
Valentić, Nataša
Ušćumlić, Gordana
Article (Published version)
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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.

Keywords:
Spirohydantoin / Absorption spectra / Crystal structure / Substituent effect / Quantum chemical calculation / Lipophilicity
Source:
Journal of Molecular Structure, 2017, 1127, 88-98
Publisher:
  • Elsevier, Amsterdam
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Zero- to Three-Dimensional Nanostructures for Application in Electronics and Renewable Energy Sources: Synthesis, Characterization and Processing (RS-45007)

DOI: 10.1016/j.molstruc.2016.07.069

ISSN: 0022-2860

WoS: 000385901800011

Scopus: 2-s2.0-84979935501
[ Google Scholar ]
6
5
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3658
Collections
  • Radovi istraživača (Inovacioni centar) / Researchers’ publications (Innovation Centre)
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Lazić, Anita
AU  - Božić, Bojan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena
AU  - Radovanović, Lidija
AU  - Valentić, Nataša
AU  - Ušćumlić, Gordana
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, Amsterdam
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
UR  - conv_5129
ER  - 
@article{
author = "Lazić, Anita and Božić, Bojan and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena and Radovanović, Lidija and Valentić, Nataša and Ušćumlić, Gordana",
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, Amsterdam",
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",
url = "conv_5129"
}
Lazić, A., Božić, B., Vitnik, V., Vitnik, Ž., Rogan, J., Radovanović, L., Valentić, N.,& Ušćumlić, G.. (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, Amsterdam., 1127, 88-98.
https://doi.org/10.1016/j.molstruc.2016.07.069
conv_5129
Lazić A, Božić B, Vitnik V, Vitnik Ž, Rogan J, Radovanović L, Valentić N, Ušćumlić G. 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
conv_5129 .
Lazić, Anita, Božić, Bojan, Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena, Radovanović, Lidija, Valentić, Nataša, Ušćumlić, Gordana, "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 .,
conv_5129 .

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