CuI-mediated synthesis of 1-aryl-5,6,7-trimethoxybenzimidazoles as potent antitubulin agents

Cong Min Peng; Shih Wei Wang; Yi Lin Hwang; Wen Chun Sun; Li Pin Chiu; Yi Ting Liu; Yu Wei Lai; Hsueh Yun Lee

doi:10.1039/d3ra01927f

CuI-mediated synthesis of 1-aryl-5,6,7-trimethoxybenzimidazoles as potent antitubulin agents

Cong Min Peng, Shih Wei Wang, Yi Lin Hwang, Wen Chun Sun, Li Pin Chiu, Yi Ting Liu, Yu Wei Lai, Hsueh Yun Lee

研究成果: 雜誌貢獻 › 文章 › 同行評審

3 引文斯高帕斯（Scopus）

摘要

In situ CuI-mediated cyclization methodology helped yield benzimidazoles with different substitution manner, such as 1,2-diarylbenzimidazoles (4 and 5) and 1-arylbenzimidazoles (6-15). The result of structure-activity relationship (SAR) study confirmed the significance of the 5,6,7-trimethoxybenzimidazole moiety, and the representative derivatives (8-10) exhibited marked antiproliferative activity against A549, HCT-116, and PC-3 cells; in addition, they are able to inhibit the polymerization of tubulin. Among them, compound 10 inhibited the growth of A549, HCT-116, and PC-3 cells with a mean IC50 value of 0.07 μM, and its IC50 value of tubulin polymerization is 0.26 μM.

原文	英語
頁（從 - 到）	13169-13176
頁數	8
期刊	RSC Advances
卷	13
發行號	19
DOIs	https://doi.org/10.1039/d3ra01927f
出版狀態	已發佈 - 4月 28 2023

ASJC Scopus subject areas

一般化學
一般化學工程

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title = "CuI-mediated synthesis of 1-aryl-5,6,7-trimethoxybenzimidazoles as potent antitubulin agents",

abstract = "In situ CuI-mediated cyclization methodology helped yield benzimidazoles with different substitution manner, such as 1,2-diarylbenzimidazoles (4 and 5) and 1-arylbenzimidazoles (6-15). The result of structure-activity relationship (SAR) study confirmed the significance of the 5,6,7-trimethoxybenzimidazole moiety, and the representative derivatives (8-10) exhibited marked antiproliferative activity against A549, HCT-116, and PC-3 cells; in addition, they are able to inhibit the polymerization of tubulin. Among them, compound 10 inhibited the growth of A549, HCT-116, and PC-3 cells with a mean IC50 value of 0.07 μM, and its IC50 value of tubulin polymerization is 0.26 μM.",

author = "Peng, {Cong Min} and Wang, {Shih Wei} and Hwang, {Yi Lin} and Sun, {Wen Chun} and Chiu, {Li Pin} and Liu, {Yi Ting} and Lai, {Yu Wei} and Lee, {Hsueh Yun}",

note = "Funding Information: This research was supported by the Ministry of Science and Technology, Taiwan (grant no. MOST111-2320-B-038-046). Taipei City Hospital (TCH-10601-62-024; TPCH-108-19). Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

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doi = "10.1039/d3ra01927f",

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T1 - CuI-mediated synthesis of 1-aryl-5,6,7-trimethoxybenzimidazoles as potent antitubulin agents

AU - Peng, Cong Min

AU - Wang, Shih Wei

AU - Hwang, Yi Lin

AU - Sun, Wen Chun

AU - Chiu, Li Pin

AU - Liu, Yi Ting

AU - Lai, Yu Wei

AU - Lee, Hsueh Yun

N1 - Funding Information: This research was supported by the Ministry of Science and Technology, Taiwan (grant no. MOST111-2320-B-038-046). Taipei City Hospital (TCH-10601-62-024; TPCH-108-19). Publisher Copyright: © 2023 The Royal Society of Chemistry.

PY - 2023/4/28

Y1 - 2023/4/28

N2 - In situ CuI-mediated cyclization methodology helped yield benzimidazoles with different substitution manner, such as 1,2-diarylbenzimidazoles (4 and 5) and 1-arylbenzimidazoles (6-15). The result of structure-activity relationship (SAR) study confirmed the significance of the 5,6,7-trimethoxybenzimidazole moiety, and the representative derivatives (8-10) exhibited marked antiproliferative activity against A549, HCT-116, and PC-3 cells; in addition, they are able to inhibit the polymerization of tubulin. Among them, compound 10 inhibited the growth of A549, HCT-116, and PC-3 cells with a mean IC50 value of 0.07 μM, and its IC50 value of tubulin polymerization is 0.26 μM.

AB - In situ CuI-mediated cyclization methodology helped yield benzimidazoles with different substitution manner, such as 1,2-diarylbenzimidazoles (4 and 5) and 1-arylbenzimidazoles (6-15). The result of structure-activity relationship (SAR) study confirmed the significance of the 5,6,7-trimethoxybenzimidazole moiety, and the representative derivatives (8-10) exhibited marked antiproliferative activity against A549, HCT-116, and PC-3 cells; in addition, they are able to inhibit the polymerization of tubulin. Among them, compound 10 inhibited the growth of A549, HCT-116, and PC-3 cells with a mean IC50 value of 0.07 μM, and its IC50 value of tubulin polymerization is 0.26 μM.

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CuI-mediated synthesis of 1-aryl-5,6,7-trimethoxybenzimidazoles as potent antitubulin agents

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