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

被引：45

作者：

Emmadi, Narender Reddy ^{[1
]}

Bingi, Chiranjeevi ^{[1
]}

Kotapalli, Sudha Sravanti ^{[2
]}

Ummanni, Ramesh ^{[2
]}

Nanubolu, Jagadeesh Babu ^{[3
]}

Atmakur, Krishnaiah ^{[1
,4
]}

机构：

[1] CSIR, Indian Inst Chem Technol, Crop Protect Chem Div, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR, Indian Inst Chem Technol, Chem Biol Div, Hyderabad 500007, Andhra Pradesh, India

[3] CSIR, Indian Inst Chem Technol, Ctr Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

[4] CSIR, Indian Inst Chem Technol, Acad Sci & Innovat Res, Hyderabad 500007, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 15期

关键词：

Antimycobacterial activity; Cytotoxicity; Click chemistry; 3-Trifluoromethyl pyrazolo-1,2,3-triazole hybrids; CLICK CHEMISTRY; TUBERCULOSIS; INHIBITORS; POTENT;

D O I：

10.1016/j.bmcl.2015.05.044

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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 (MC2 155) and also verified the cytotoxicity. These studies engendered promising lead compounds 5q, 7b and 7c with MIC (mu g/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. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2918 / 2922

页数：5

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