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

doi:10.6023/cjoc201807019

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

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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

刘战雄^a, 袁晶^a, 张振锋^b, 颜德岳^a, 张万斌^a,b

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 E-mail:wanbin@sjtu.edu.cn;zhenfeng@sjtu.edu.cn
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

Liu Zhanxiong^a, Yuan Jing^a, Zhang Zhenfeng^b, Yan Deyue^a, Zhang Wanbin^a,b

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 E-mail:wanbin@sjtu.edu.cn;zhenfeng@sjtu.edu.cn
Supported by:
Project supported by the National Key Research and Development Plan (No. 2016YFA0201500) and the National Natural Science Foundation of China (No. 21572131).

1. 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.PDF(4610KB)

Abstract

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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Liu Zhanxiong, Yuan Jing, Zhang Zhenfeng, Yan Deyue, Zhang Wanbin. 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[J]. Chin. J. Org. Chem., 2018, 38(12): 3302-3317.

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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

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

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