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
Samo za registrovane korisnike
2017
Autori
Lazić, Anita M.Božić, Bojan
Vitnik, Vesna
Vitnik, Željko
Rogan, Jelena R.
Radovanović, Lidija D.
Valentić, Nataša V.
Ušćumlić, Gordana
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Spirohydantoin / Absorption spectra / Crystal structure / Substituent effect / Quantum chemical calculation / LipophilicityIzvor:
Journal of Molecular Structure, 2017, 1127, 88-98Izdavač:
- Elsevier
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-172013)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-172035)
- 0-3D nanostrukture za primenu u elektronici i obnovljivim izvorima energije: sinteza, karakterizacija i procesiranje (RS-45007)
DOI: 10.1016/j.molstruc.2016.07.069
ISSN: 0022-2860
WoS: 000385901800011
Scopus: 2-s2.0-84979935501
Institucija/grupa
IHTMTY - JOUR AU - Lazić, Anita M. AU - Božić, Bojan AU - Vitnik, Vesna AU - Vitnik, Željko AU - Rogan, Jelena R. AU - Radovanović, Lidija D. AU - Valentić, Nataša V. AU - Ušćumlić, Gordana PY - 2017 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2073 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 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 VL - 1127 SP - 88 EP - 98 DO - 10.1016/j.molstruc.2016.07.069 ER -
@article{ author = "Lazić, Anita M. and Božić, Bojan and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena R. and Radovanović, Lidija D. and Valentić, Nataša V. 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", 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", volume = "1127", pages = "88-98", doi = "10.1016/j.molstruc.2016.07.069" }
Lazić, A. M., Božić, B., Vitnik, V., Vitnik, Ž., Rogan, J. R., Radovanović, L. D., Valentić, N. V.,& 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., 1127, 88-98. https://doi.org/10.1016/j.molstruc.2016.07.069
Lazić AM, Božić B, Vitnik V, Vitnik Ž, Rogan JR, Radovanović LD, Valentić NV, 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 .
Lazić, Anita M., Božić, Bojan, Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena R., Radovanović, Lidija D., Valentić, Nataša V., 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 . .