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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

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2017
Authors
Lazić, Anita M.
Božić, Bojan
Vitnik, Vesna
Vitnik, Željko
Rogan, Jelena R.
Radovanović, Lidija D.
Valentić, Nataša V.
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
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
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2073
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IHTM

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