QSAR study and conformational analysis of 4-arylthiazolylhydrazones derived from 1-indanones with anti-Trypanosoma cruzi activity

[Display omitted] A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations:...

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Bibliographic Details
Published in:European journal of pharmaceutical sciences 2015-10, Vol.78, p.190-197
Main Authors: Noguera, Guido J., Fabian, Lucas E., Lombardo, Elisa, Finkielsztein, Liliana
Format: Article
Language:English
Subjects:
Anti-trypanosomal activity
Antiprotozoal Agents - chemistry
Antiprotozoal Agents - pharmacology
Chagas disease
Conformational analysis
Hydrazones - chemistry
Hydrazones - pharmacology
Indans - chemistry
Molecular Conformation
QSAR
Quantitative Structure-Activity Relationship
Thiazolylhydrazones
Trypanosoma cruzi - drug effects
Trypanosoma cruzi - growth & development
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Summary:[Display omitted] A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations: cis (A, B and C) and trans. The possible bioactive conformation was selected by a 3D-QSAR model. Different molecular parameters were calculated to produce QSAR second-generation models. These QSAR results are discussed in conjunction with conformational analysis from molecular modeling studies. The main factor to determine the activity of the compounds was the partial charge at the N(3) atom (qN3). The predictive ability of the QSAR equations proposed was experimentally validated. The QSAR models developed in this study will be helpful to design novel potent TZHs.
ISSN:0928-0987
1879-0720
DOI:10.1016/j.ejps.2015.07.014