Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

Ailong Shi; Defa Wang; He Wang; Yue Wu; Haiqiu Tian; Qi Guan; Kai Bao; Weige Zhang

doi:10.1039/C6RA24651F

Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

Ailong Shi,^a^b Defa Wang,^a He Wang,^a Yue Wu,^a Haiqiu Tian,^a Qi Guan,*^b Kai Bao*^a and Weige Zhang*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China
E-mail: zhangweige@syphu.edu.cn, baokai@syphu.edu.cn

^b School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China
E-mail: guanqi@syphu.edu.cn
Fax: +86 2423986393
Tel: +86 24 23986422

Abstract

A series of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acids/carbohydrazides as analogues of febuxostat were synthesized and evaluated for their in vitro xanthine oxidase (XO) inhibitory activity. Among these compounds, the carboxylic acid derivatives 7a–h and 8a–h exhibited high potency in the submicromolar/nanomolar range. Steady-state kinetics experiment revealed that 7f was a mixed-type inhibitor of xanthine oxidase. In addition, a molecular docking study of 7f was performed to determine its binding mode at the active site of xanthine oxidase.

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Publication details

The article was received on 03 Oct 2016, accepted on 30 Nov 2016 and first published on 12 Dec 2016

Article type: Paper

DOI: 10.1039/C6RA24651F

Citation: RSC Adv., 2016,6, 114879-114888

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Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

A. Shi, D. Wang, H. Wang, Y. Wu, H. Tian, Q. Guan, K. Bao and W. Zhang, RSC Adv., 2016, 6, 114879
DOI: 10.1039/C6RA24651F
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Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

Abstract

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Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

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