Citation: 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 shu

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

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

Corresponding author: Zhang Zhenfeng, zhenfeng@sjtu.edu.cn Zhang Wanbin, wanbin@sjtu.edu.cn
Received Date: 9 July 2018
Revised Date: 3 August 2018
Available Online: 14 December 2019
Fund Project: the National Natural Science Foundation of China 21572131Project supported by the National Key Research and Development Plan (No. 2016YFA0201500) and the National Natural Science Foundation of China (No. 21572131)the National Key Research and Development Plan 2016YFA0201500

Figures(7)

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).
- anthraquinone,
- naphthoquinone,
- imidazole,
- antitumor
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

References

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通讯作者: 陈斌, bchen63@163.com