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Synthesis, In Vitro Antitubercular Activity and 3D‐QSAR of Novel Quinoxaline Derivatives
Author(s) -
Puratchikody Ayarivan,
Natarajan Ramalakshmi,
Jayapal Mohanapriya,
Doble Mukesh
Publication year - 2011
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/j.1747-0285.2011.01246.x
Subject(s) - quinoxaline , chemistry , in vitro , quantitative structure–activity relationship , mycobacterium tuberculosis , steric effects , stereochemistry , nitro , isoniazid , combinatorial chemistry , loo , biochemistry , organic chemistry , tuberculosis , medicine , alkyl , pathology
Twenty new quinoxalines bearing azetidinone and thiazolidinone groups were synthesized by cyclocondensation of Schiff bases of quinoxaline‐2, 3‐dione and were characterized with several analytical tools. They were tested against Mycobacterium tuberculosis H37Rv at a concentration of 10 μg/mL by Microplate Alamar Blue Assay method. Quinoxaline derivatives with 2‐chloro, dimethylamino and nitro substitutions exhibited in vitro activity, comparable to that of the drug, isoniazid. Three‐dimensional quantitative structure–activity relationship studies indicated that electrostatic and steric field descriptors could explain the observed activity. The developed model fits the data well and has good predictive capability ( r 2 = 0.81, q 2 = 0.71, F = 27.06, r 2 _pred = 0.84, r 2 m = 0.84, r 2 BS = 0.80). Electronegative groups play an important role in the antitubercular activity.