1-单取代萘醌及蒽醌并咪唑衍生物的设计合成和抗肿瘤活性研究
收稿日期: 2018-07-09
修回日期: 2018-08-03
网络出版日期: 2018-08-14
基金资助
国家重点研发计划（No.2016YFA0201500）和国家自然科学基金（No.21572131）资助项目.
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
Received date: 2018-07-09
Revised date: 2018-08-03
Online published: 2018-08-14
Supported by
Project supported by the National Key Research and Development Plan (No. 2016YFA0201500) and the National Natural Science Foundation of China (No. 21572131).
刘战雄 , 袁晶 , 张振锋 , 颜德岳 , 张万斌 . 1-单取代萘醌及蒽醌并咪唑衍生物的设计合成和抗肿瘤活性研究[J]. 有机化学, 2018 , 38(12) : 3302 -3317 . DOI: 10.6023/cjoc201807019
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
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