Design, Synthesis and Antitumor Activity of 1-Monosubstituted 1H-Naphtho[2,3-d]imidazole-4,9-diones and 1H-Anthra[2,3-d]imidazole-4,11-diones

作者：Liu, Zhanxiong; Yuan, Jing; Zhang, Zhenfeng^*; Yan, Deyue; Zhang, Wanbin^*

来源：Chinese Journal of Organic Chemistry, 2018, 38(12): 3302-3317.

DOI：10.6023/cjoc201807019

• anthraquinone
• naphthoquinone
• imidazole antitumor

In order to further expand the molecular diversity of quinone-fused imidazoles as anticancer agents, a number of 1-monosubstituted 1H-naphtho[2,3-d]imidazole-4,9-diones and 1H-anthra[2,3-d]imidazole-4,11-diones were designed, synthesized and biologically evaluated. The structure-activity relationships were studied in vitro against three human cancer cell lines (human breast carcinoma cell line MCF-7, human cervical carcinoma cell line Hela and human lung carcinoma cell line A549) and one normal cell line (mouse fibroblast cell line L929). Among them, 1-methyl-1H-anthra[2,3- d]imidazole-4,11-diones, which bears a large pi-system and a small N-substituent in the imidazole segment, showed good antiproliferative activity against MCF-7 and A549 (IC50 values are 7.4 and 1.6 mu mol.L--(1), respectively) and almost no cytotoxicitv to L929 (IC50 is 150 mu mol.L-1).

• 出版日期2018-12-25
• 单位上海交通大学