Issue 19, 2023
From the journal:

RSC Advances

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

Cong-Min Peng,‡a   Shih-Wei Wang, ORCID logo ‡bcd   Yi-Lin Hwang,a   Wen-Chun Sun,be   Li-Pin Chiu,fg   Yi-Ting Liu,a   Yu-Wei Lai*hi  and  Hsueh-Yun Lee ORCID logo *ajk  

* Corresponding authors

a School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei, Taiwan
E-mail: hyl@tmu.edu.tw

b Institute of Biomedical Sciences, MacKay Medical College, New Taipei City, Taiwan

c Department of Medicine, MacKay Medical College, New Taipei City, Taiwan

d School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

e Division of Colon and Rectal Surgery, Department of Surgery, MacKay Memorial Hospital, Taipei, Taiwan

f Division of General Surgery, Taipei City Hospital Chushing Branch, Taipei, Taiwan

g General Education Center, University of Taipei, Taipei, Taiwan

h Division of Urology, Taipei City Hospital Renai Branch, Taipei, Taiwan

i Department of Urology, School of Medicine and Shu-Tien Urological Science Research Center, National Yang Ming Chiao Tung University, Taipei, Taiwan

j PhD Program in Drug Discovery and Development Industry, College of Pharmacy, Taipei Medical University, Taipei, Taiwan

k TMU Research Center of Cancer Translational Medicine, Taipei Medical University, Taipei, Taiwan

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.

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

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Article information

DOI
https://doi.org/10.1039/D3RA01927F
Article type
Paper
Submitted
24 Mar 2023
Accepted
17 Apr 2023
First published
28 Apr 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 13169-13176

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

C. Peng, S. Wang, Y. Hwang, W. Sun, L. Chiu, Y. Liu, Y. Lai and H. Lee, RSC Adv., 2023, 13, 13169 DOI: 10.1039/D3RA01927F

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