Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3302-3317.DOI: 10.6023/cjoc201807019 Previous Articles     Next Articles



刘战雄a, 袁晶a, 张振锋b, 颜德岳a, 张万斌a,b   

  1. a 上海交通大学化学化工学院 上海市手性药物分子工程重点实验室 上海 200240;
    b 上海交通大学药学院 上海 200240
  • 收稿日期:2018-07-09 修回日期:2018-08-03 发布日期:2018-08-14
  • 通讯作者: 张万斌, 张振锋;
  • 基金资助:


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

Liu Zhanxionga, Yuan Jinga, Zhang Zhenfengb, Yan Deyuea, Zhang Wanbina,b   

  1. a Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240;
    b School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2018-07-09 Revised:2018-08-03 Published:2018-08-14
  • Contact: 10.6023/cjoc201807019;
  • Supported by:

    Project supported by the National Key Research and Development Plan (No. 2016YFA0201500) and the National Natural Science Foundation of China (No. 21572131).

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-dione, which bears a large π-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 μmol·L-1, respectively) and almost no cytotoxicity to L929 (IC50 is 150 μmol·L-1).

Key words: anthraquinone, naphthoquinone, imidazole, antitumor