title: Synthesis, in vitro antitubercular activity and 3D-QSAR of novel quinoxaline derivatives.
abstract: 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 (r² = 0.81, q² = 0.71, F = 27.06, r² _pred = 0.84, r²(m) = 0.84, r² BS = 0.80). Electronegative groups play an important role in the antitubercular activity.
authors.affiliation: Department of Pharmaceutical Technology, Anna University Tiruchirappalli, Tiruchirappalli 620024, Tamilnadu, India.
authors.forename: Ayarivan
authors.initials: A
authors.lastname: Puratchikody
authors.forename: Ramalakshmi
authors.initials: R
authors.lastname: Natarajan
authors.forename: Mohanapriya
authors.initials: M
authors.lastname: Jayapal
authors.forename: Mukesh
authors.initials: M
authors.lastname: Doble
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D021281:Quantitative Structure-Activity Relationship; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012545:Schiff Bases / Q000737:chemistry
chemical_list: D000995:Antitubercular Agents; D011810:Quinoxalines; D012545:Schiff Bases