title: Synthesis and evaluation of novel fluorinated pyrazolo-1,2,3-triazole hybrids as antimycobacterial agents.
abstract: A library of novel 3-trifluoromethyl pyrazolo-1,2,3-triazole hybrids (5-7) were accomplished starting from 5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-amine (1) via key intermediate 2-azido-N-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)acetamide (3) through click chemistry approach. Thus obtained compounds in 5-7 series were evaluated for in vitro antimycobacterial activity against Mycobacterium smegmatis (MC(2) 155) and also verified the cytotoxicity. These studies engendered promising lead compounds 5q, 7b and 7c with MIC (μg/mL) values 15.34, 16.18 and 16.60, respectively. Amongst these three compounds, 2-(4-(4-methoxybenzoyl)-1H-1,2,3-triazol-1-yl)-N-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl) acetamide (5q) emerged as the most promising antitubercular agent with lowest cytotoxicity against the A549 cancer cell line. This is the first report to demonstrate the pyrazolo triazole hybrids as potential antimycobacterial agents.
authors.affiliation: Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Narender Reddy
authors.initials: NR
authors.lastname: Emmadi
authors.affiliation: Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Chiranjeevi
authors.initials: C
authors.lastname: Bingi
authors.affiliation: Chemical Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Sudha Sravanti
authors.initials: SS
authors.lastname: Kotapalli
authors.affiliation: Chemical Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Ummanni
authors.affiliation: Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Jagadeesh Babu
authors.initials: JB
authors.lastname: Nanubolu
authors.affiliation: Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research, CSIR- Indian Institute of Chemical Technology, Hyderabad 500007, India. Electronic address: krishnu@iict.res.in.
authors.forename: Krishnaiah
authors.initials: K
authors.lastname: Atmakur
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D057930:Click Chemistry; D054879:Halogenation; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D009165:Mycobacterium Infections, Nontuberculous / Q000188:drug therapy; D020102:Mycobacterium smegmatis / Q000187:drug effects*; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D011720:Pyrazoles; D014230:Triazoles; C031280:pyrazole
keywords: 3-Trifluoromethyl pyrazolo-1,2,3-triazole hybrids; Antimycobacterial activity; Click chemistry; Cytotoxicity