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

4 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

Access to Document

10.1039/d3ra01927f

Cite this

@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",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "19",

}

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 - http://www.scopus.com/inward/record.url?scp=85159119843&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85159119843&partnerID=8YFLogxK

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this