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Chromanyl–isoxazolidines as Antibacterial agents: Synthesis, Biological Evaluation, Quantitative Structure Activity Relationship, and Molecular Docking Studies
Author(s) -
Singh Gagandeep,
Sharma Anuradha,
Kaur Harpreet,
Ishar Mohan Paul S.
Publication year - 2016
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12653
Subject(s) - chemistry , antibacterial activity , docking (animal) , minimum inhibitory concentration , staphylococcus aureus , quantitative structure–activity relationship , stereochemistry , in vitro , salmonella , combinatorial chemistry , biochemistry , bacteria , biology , medicine , genetics , nursing
Regio‐ and stereoselective 1,3‐dipolar cycloadditions of C ‐(chrom‐4‐one‐3‐yl)‐ N ‐phenylnitrones ( N ) with different mono‐substituted, disubstituted, and cyclic dipolarophiles were carried out to obtain substituted N ‐phenyl‐3′‐(chrom‐4‐one‐3‐yl)‐isoxazolidines ( 1‐40 ). All the synthesized compounds were assayed for their in vitro antibacterial activity and display significant inhibitory potential; in particular, compound 32 exhibited good inhibitory activity against Salmonella typhymurium‐ 1 & Salmonella typhymurium‐ 2 with minimum inhibitory concentration value of 1.56 μ g/mL and also showed good potential against methicillin‐resistant Staphylococcus aureus with minimum inhibitory concentration 3.12 μ g/mL. Quantitative structure activity relationship investigations with stepwise multiple linear regression analysis and docking simulation studies have been performed for validation of the observed antibacterial potential of the investigated compounds for determination of the most important parameters regulating antibacterial activities.