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

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	13169-13176
Number of pages	8
Journal	RSC Advances
Volume	13
Issue number	19
DOIs	https://doi.org/10.1039/d3ra01927f
Publication status	Published - Apr 28 2023

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1039/d3ra01927f

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@article{507ca0589e644795be934a5aed7a4df5,

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.",

year = "2023",

month = apr,

day = "28",

doi = "10.1039/d3ra01927f",

language = "English",

volume = "13",

pages = "13169--13176",

journal = "RSC Advances",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/85159119843

UR - https://www.scopus.com/pages/publications/85159119843#tab=citedBy

U2 - 10.1039/d3ra01927f

DO - 10.1039/d3ra01927f

M3 - Article

AN - SCOPUS:85159119843

SN - 2046-2069

VL - 13

SP - 13169

EP - 13176

JO - RSC Advances

JF - RSC Advances

IS - 19

ER -

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

Abstract

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