碘化亚铜介导合成1-芳基-5,6,7-三甲氧基苯并咪唑作为有效的抗微管蛋白剂。
CuI-mediated synthesis of 1-aryl-5,6,7-trimethoxybenzimidazoles as potent antitubulin agents.
作者信息
Peng Cong-Min, Wang Shih-Wei, Hwang Yi-Lin, Sun Wen-Chun, Chiu Li-Pin, Liu Yi-Ting, Lai Yu-Wei, Lee Hsueh-Yun
机构信息
School of Pharmacy, College of Pharmacy, Taipei Medical University Taipei Taiwan
Institute of Biomedical Sciences, MacKay Medical College New Taipei City Taiwan.
出版信息
RSC Adv. 2023 Apr 28;13(19):13169-13176. doi: 10.1039/d3ra01927f. eCollection 2023 Apr 24.
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 IC value of 0.07 μM, and its IC value of tubulin polymerization is 0.26 μM.
碘化亚铜介导的环化方法有助于生成具有不同取代方式的苯并咪唑，例如1,2 - 二芳基苯并咪唑（4和5）以及1 - 芳基苯并咪唑（6 - 15）。构效关系（SAR）研究结果证实了5,6,7 - 三甲氧基苯并咪唑部分的重要性，代表性衍生物（8 - 10）对A549、HCT - 116和PC - 3细胞表现出显著的抗增殖活性；此外，它们能够抑制微管蛋白的聚合。其中，化合物10抑制A549、HCT - 116和PC - 3细胞生长的平均IC值为0.07 μM，其对微管蛋白聚合的IC值为0.
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