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Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as novel microtubule destabilizers.

ABSTRACT: A series of 1-aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as microtubule destabilizers were designed, synthesised and evaluated for anticancer activity. Based on bioisosterism, we introduced the tetrazole moiety containing the hydrogen-bond acceptors as B-ring of XRP44X analogues. The key intermediates ethyl 1-aryl-1H-tetrazole-5-carboxylates 10 can be simply and efficiently prepared via a microwave-assisted continuous operation process. Among the compounds synthesised, compound 6-31 showed noteworthy potency against SGC-7901, A549 and HeLa cell lines. In mechanism studies, compound 6-31 inhibited tubulin polymerisation and disorganised microtubule in SGC-7901 cells by binding to tubulin. Moreover, compound 6-31 arrested SGC-7901cells in G2/M phase. This study provided a new perspective for development of antitumor agents that target tubulin.

SUBMITTER: Wang C 

PROVIDER: S-EPMC8759721 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1<i>H</i>-tetrazols as novel microtubule destabilizers.

Wang Chao C   Li Yuelin Y   Liu Zi Z   Wang Zeyu Z   Liu Zihan Z   Man Shuai S   Zhang Yujing Y   Bao Kai K   Wu Yingliang Y   Guan Qi Q   Zuo Daiying D   Zhang Weige W  

Journal of enzyme inhibition and medicinal chemistry 20211201 1

A series of 1-aryl-5-(4-arylpiperazine-1-carbonyl)-1<i>H</i>-tetrazols as microtubule destabilizers were designed, synthesised and evaluated for anticancer activity. Based on bioisosterism, we introduced the tetrazole moiety containing the hydrogen-bond acceptors as B-ring of XRP44X analogues. The key intermediates ethyl 1-aryl-1<i>H</i>-tetrazole-5-carboxylates <b>10</b> can be simply and efficiently prepared <i>via</i> a microwave-assisted continuous operation process. Among the compounds synt  ...[more]

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