New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents
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2011
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Abstract
Three new series of quinoline-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines were synthesized through multi-step reactions. The required intermediate, [1-(6-methoxy-2-methylquinolin-4-yl)-1H-1, 2,3-triazol-4-yl]methanol (2) was prepared by treating 4-azido-6-methoxy-2- methylquinoline (1) with propargyl alcohol. Three different series of compounds were synthesized from this intermediate. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 2 was confirmed by X-ray crystallographic study. Further, the title compounds were evaluated for their in vitro anti-bacterial activity against five different bacterial strains and antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis (ATCC 19420) and Mycobacterium fortuitum (ATCC 19542). Title compounds, 6a, 6d, 6i, 6j, 7e, 10a and 10i were found to be active against Mycobacterium tuberculosis H37Rv strain and could be lead molecules of interest. © 2011 Elsevier Masson SAS.
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1 [1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methanamine, 1,2,3 triazole derivative, 2 chloro n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]benzamide, 2 fluoro n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]benzamide, 3,4 dichloro n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1-3]triazol 4 ylmethyl]benzenesulfonamide, 4 [4 (azidomethyl) 1h 1,2,3 triazol 1 yl] 6 methoxy 2 methylquinoline, 4 ethyl n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1,2,3]triazol 4 ylmethyl]benzenesulfonamide, 4 ethyl n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]benzamide, 4 fluoro n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1,2,3]triazol 4 methyl]benzenesulfonamide, 4 methoxy n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1,2,3]triazol 4 ylmethyl]benzenesulfonamide, 4 methoxy n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]benzamide, 6 methoxy 2 methyl 4 [4 (piperazin 1 ylmethyl) 1h 1,2,3 triazol 1 yl]quinoline, [1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methanol, [1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl methanesulfonate, amide, fluoro n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]benzamide, n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1,2,3]triazol 4 ylmethyl] 2 trifluoro methyl benzenesulfonamide, n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1,2,3]triazol 4 ylmethyl] 4 methyl benzenesulfonamide, n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1,2,3]triazol 4 ylmethyl] 4 trifluoromethyl benzamide, n [1 (6 methoxy 2 methyl quinolin 4 yl) 1h [1-3]triazol 4 ylmethyl]benzene sulfonamide, n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl] 4 methylbenzamide, n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]acetamide, n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]cyclo butanecarboxamide, n [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]cyclopro panecarboxamide, piperazine derivative, quinoline derivative, sulfonamide, tert butyl 4 [[1 (6 methoxy 2 methylquinolin 4 yl) 1h 1,2,3 triazol 4 yl]methyl]piperazine 1 carboxylate, tuberculostatic agent, unclassified drug, unindexed drug, antibacterial activity, article, bacterial strain, controlled study, drug structure, drug synthesis, in vitro study, Mycobacterium fortuitum, Mycobacterium smegmatis, Mycobacterium tuberculosis, nonhuman, X ray crystallography, Amides, Antitubercular Agents, Crystallography, X-Ray, Dose-Response Relationship, Drug, Escherichia coli, Microbial Sensitivity Tests, Models, Molecular, Molecular Structure, Piperazines, Pseudomonas, Quinolines, Stereoisomerism, Streptococcus, Structure-Activity Relationship, Triazoles
Citation
European Journal of Medicinal Chemistry, 2011, 46, 6, pp. 2503-2512