2. Academic Validation
  3. Synthesis and evaluation of novel fluorinated pyrazolo-1,2,3-triazole hybrids as antimycobacterial agents

Synthesis and evaluation of novel fluorinated pyrazolo-1,2,3-triazole hybrids as antimycobacterial agents

  • Bioorg Med Chem Lett. 2015 Aug 1;25(15):2918-22. doi: 10.1016/j.bmcl.2015.05.044.
Narender Reddy Emmadi 1,  Chiranjeevi Bingi 1,  Sudha Sravanti Kotapalli 2,  Ramesh Ummanni 2,  Jagadeesh Babu Nanubolu 3,  Krishnaiah Atmakur 4
Affiliations

Affiliations

  • 1 Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
  • 2 Chemical Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
  • 3 Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
  • 4 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.
PMID: 26048808 DOI: 10.1016/j.bmcl.2015.05.044
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.

Keywords

3-Trifluoromethyl pyrazolo-1,2,3-triazole hybrids; Antimycobacterial activity; Click chemistry; Cytotoxicity.

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