title: Design, synthesis and 3D-QSAR studies of new diphenylamine containing 1,2,4-triazoles as potential antitubercular agents.
abstract: A new series of new diphenylamine containing 1,2,4-triazoles were synthesized from 4-arylideneamino-5-[2-(2,6-dichlorophenylamino) benzyl]-2H-1,2,4-triazole-3(4H)-thiones 3a-f. The synthesized compounds were screened for in-vitro antimycobacterial and antibacterial activities. The synthesized compounds 4a, 4e and 4d have shown potential activity against Mycobacterium tuberculosis H37Rv strain with MIC of 0.2, 1.6 and 3.125 μM respectively. To investigate the SAR of diphenylamine containing 1,2,4-triazole derivatives in more details, CoMFA (q(2)-0.432, r(2)-0.902) and CoMSIA (q(2)-0.511, r(2)-0.953) models on M. tuberculosis H37Rv were established. The generated 3D-QSAR models are externally validated and have shown significant statistical results, and these models can be used for further rational design of novel diphenylamine containing 1,2,4-triazoles as potent antitubercular agents.
authors: Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Mysore 570015, Karnataka, India.
authors: K
authors: K
authors: Mohan Krishna
authors: Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Mysore 570015, Karnataka, India.
authors: Bharathkumar
authors: B
authors: Inturi
authors: Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Mysore 570015, Karnataka, India. Electronic address: gbrpujar@gmail.com.
authors: Gurubasavaraj V
authors: GV
authors: Pujar
authors: Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Mysore 570015, Karnataka, India.
authors: Madhusudan N
authors: MN
authors: Purohit
authors: Department of Microbiology, JSS Medical College, JSS University, Mysore 570015, Karnataka, India.
authors: G S
authors: GS
authors: Vijaykumar
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D002522:Chlorocebus aethiops; D004159:Diphenylamine / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D056945:Hep G2 Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*; D014709:Vero Cells
chemical_list: D000900:Anti-Bacterial Agents; D014230:Triazoles; C045575:1,2,4-triazole; D004159:Diphenylamine
keywords: 1,2,4-Triazoles; 3D-QSAR; CoMFA; CoMSIA; MABA assay; Mycobacterium tuberculosis