Nayak, N.Ramprasad, J.Udayakumar, U.2026-02-052017Journal of Heterocyclic Chemistry, 2017, 54, 1, pp. 171-1820022152Xhttps://doi.org/10.1002/jhet.2564https://idr.nitk.ac.in/handle/123456789/25839The article describes the design, synthesis, and characterization of a new series of 8-trifluoromethylquinoline substituted pyrazole-3-carboxamides (9a, 9b, 9c, 9d, 9e, 9f, 9g, 9h, 9i, 9j, 9k, 9l, 9m, 9n, 9o, 9p, 9q, 9r, 9s, 9t) derived from different primary and secondary amines. The intermediate and target compounds were characterized using spectroscopic methods. The structures of intermediate 7 and target molecule 9d were evidenced by the single crystal X-ray study. All the synthesized target compounds (9a, 9b, 9c, 9d, 9e, 9f, 9g, 9h, 9i, 9j, 9k, 9l, 9m, 9n, 9o, 9p, 9q, 9r, 9s, 9t) and three intermediates (6, 7, 8) were screened for their in vitro antitubercular activity against Mycobacterium tuberculosis H<inf>37</inf>Rv strain. Two compounds, 9k and 9t, showed significant inhibition activity with MIC of 3.13 µg/mL, which is comparable with the activity of standard drug, ethambutol. The carboxamides derived from benzylamine derivatives were more active than their aniline analogs. In general, the hybrid amides with a N-methylene linkage (-CONHCH<inf>2</inf>-) exhibited enhanced antitubercular activity. In the antibacterial screening, intermediate 3-hydrazinyl-2-methyl-8-(trifluoromethyl)quinoline (6) displayed remarkable activity against the tested bacterial strains. Further, the active anti-TB derivatives were non-toxic to benign NIH 3T3 cells, which demonstrate the lack of general cellular toxicity and hence signifies their suitability for further lead development. © 2015 HeteroCorporation(2,6 dimethylmorpholino)[1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazol 3 yl]methanone1 [2 methyl 8 (trifluoromethyl) 4 quinolyl] 5 (3 pyridyl) n [[4 (trifluoromethoxy)phenyl]methyl]pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl) 4 quinolyl] 5 (3 pyridyl) n [[4 (trifluoromethyl)phenyl]methyl]pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl) 4 quinolyl] n (4 tolylmethyl) 5 (3 pyridyl)pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) n (2,2,2 trifluoroethyl) 1h pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) n 3 tolyl 1h pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) n 4 tolyl 1h pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) n [3 (trifluoromethyl)phenyl] 1h pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) n [4 (trifluoromethoxy)phenyl] 1h pyrazole 3 carboxamide1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) n [4 (trifluoromethyl)phenyl] 1h pyrazole 3 carboxamideamideantibiotic agentciprofloxacinethambutolisoniazidn (4 fluorophenyl) 1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazole 3 carboxamiden (4 methoxyphenyl) 1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazole 3 carboxamiden (cyclopropylmethyl) 1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazole 3 carboxamiden cyclopropyl 1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazole 3 carboxamiden tert butyl 1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazole 3 carboxamiden [(4 fluorophenyl)methyl] 1 [2 methyl 8 (trifluoromethyl) 4 quinolyl] 5 (3 pyridyl)pyrazole 3 carboxamiden [(4 methoxyphenyl)methyl] 1 [2 methyl 8 (trifluoromethyl) 4 quinolyl] 5 (3 pyridyl)pyrazole 3 carboxamidepyrazinamidepyrazole derivativequinoline derivativetuberculostatic agentunclassified drug[1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazol 3 yl](4 methyl piperidin 1 yl)methanone[1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazol 3 yl](morpholino)methanone[1 [2 methyl 8 (trifluoromethyl)quinolin 4 yl] 5 (pyridin 3 yl) 1h pyrazol 3 yl](piperidin 1 yl)methanone3T3 cell lineantibacterial activityArticlebacterial growthbacterial straincomparative studycontrolled studydrug cytotoxicitydrug designdrug screeningdrug structuredrug synthesisEscherichia coliin vitro studyminimum inhibitory concentrationMycobacterium tuberculosisnonhumanPseudomonas aeruginosaStaphylococcus aureusX ray crystallography