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3,4‐Disubstituted‐1,2,3,4,5,6,7,8‐octahydroquinazoline‐2‐thiones: Synthesis, Antimicrobial Evaluation and QSAR Investigations Using Hansch Analysis
Author(s) -
Minu Maninder,
Thangadurai Ananda,
Wakode Sharad R.,
Agrawal Shyam S.,
Narasimhan Balasubramanian
Publication year - 2008
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200700153
Subject(s) - quantitative structure–activity relationship , antimicrobial , chemistry , candida albicans , antifungal , topological index , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , microbiology and biotechnology , biology
The 3,4‐disubstituted‐1,2,3,4,5,6,7,8‐octahydroquinazoline‐2‐thione derivatives were synthesized and characterized by physicochemical and spectral means, and the results of antimicrobial study of these compounds against Staphylococcus aureus, Escherichia coli, and Candida albicans by tube dilution method indicated that 4‐(4‐chlorophenyl)‐3‐(4‐nitrophenylsulfonyl)‐1,2,3,4,5,6,7,8‐octahydroquinazoline‐2‐thione 6 and 4‐(4‐fluorophenyl)‐3‐(4‐nitrophenylsulfonyl)‐1,2,3,4,5,6,7,8‐octahydroquinazoline‐2‐thione 12 were the most potential ones. Further, the QSAR studies by Hansch analysis applied to find out the correlation between physicochemical characteristics of synthesized compounds with antimicrobial activity demonstrated the contribution of electronic parameter, total energy (Te) and the topological parameter (valence second order molecular connectivity index ( 2 χ v )). Excellent statistically significant models were developed by Hansch approach (r 2 = 0.828–0.898) for the three microorganisms under study. The cross‐validated r 2 (q 2 ), which is an indication of the predictive capability of the model for all cases was also very good (q 2 = 0.776–0.875).