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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 12: 3302 - 3317

DOI: https://doi.org/10.6023/cjoc201807019

Articles

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 ,
  • Yuan Jing ,
  • Zhang Zhenfeng ,
  • Yan Deyue ,
  • Zhang Wanbin
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  • 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 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).

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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

Cite this article

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]. Chinese Journal of Organic Chemistry, 2018 , 38(12) : 3302 -3317 . DOI: 10.6023/cjoc201807019

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