Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts

doi:10.6023/cjoc201610043

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1506-1515.DOI: 10.6023/cjoc201610043 Previous Articles Next Articles

Articles

吲哚并四氢呋喃-咪唑盐杂合物的合成及细胞毒活性研究

刘正芬^a, 张朝波^a, 段胜祖^a, 刘洋^a, 陈文^a, 李艳^b, 张洪彬^a, 羊晓东^a

a. 云南大学教育部自然资源药物化学重点实验室昆明 650091;
b. 中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室昆明 650204

收稿日期:2016-10-28 修回日期:2017-01-12 发布日期:2017-01-20
通讯作者: 羊晓东,张洪彬 E-mail:xdyang@ynu.edu.cn;zhanghb@ynu.edu.cn
基金资助:
国家自然科学基金（Nos.21662043，21462049，U1402227，21332007）、长江学者和创新团队发展计划（No.IRT13095）、云南省自然科学基金（No.2013FA028）资助项目.

Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts

Liu Zhengfen^a, Zhang Chaobo^a, Duan Shengzu^a, Liu Yang^a, Chen Wen^a, Li Yan^b, Zhang Hongbin^a, Yang Xiaodong^a

a. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 65009;
b. State Key Laboratory for Phytochemistry and Plant Resources in West China, Kunming Institute of Botany,Chinese Academy of Science, Kunming 650204

Received:2016-10-28 Revised:2017-01-12 Published:2017-01-20
Contact: 10.6023/cjoc201610043 E-mail:xdyang@ynu.edu.cn;zhanghb@ynu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21662043, 21462049, U1402227, 21332007), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT13095), the Natural Science Foundation of Yunnan Province (No. 2013FA028).

1. Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts.PDF(1974KB)

Abstract

A series of novel hybrid compounds between indolo[b]tetrahydrofuran and imidazolium salts were prepared from tryptophol by four steps of Sharpless epoxidation, amidation, coupling and salt formation. Their structures were confirmed by ¹H NMR, ¹³C NMR, HRMS and X-ray crystallographic analysis. These compounds were evaluated in vitro against a panel of human tumor cell lines. The results showed that 1-((3aR,8aS)-3,3a-dihydro-3a-hydroxy-2H-furo[2,3-b]indol-8(8aH)-yl)etha-none-3-(2-(naphthalen-2-yl)-2-oxoethyl)-5,6-dimethyl-1H-benzo[d]-imidazol-3-ium bromide (20) and 1-((3aR,8aS)-3,3a-di-hydro-3a-hydroxy-2H-furo[2,3-b]indol-8(8aH)-yl)ethanone-3-(2-naphthylmethyl)-5,6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (22) exhibited higher inhibitory activity selectively against SMMC-7721, MCF-7 and SW480 cell lines compared with DDP. In particular, 1-((3aR,8aS)-3,3a-dihydro-3a-hydroxy-2H-furo[2,3-b]indol-8(8aH)-yl)ethanone-3-(2-bromobenzyl)-5,6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (24) was more selective to SW-480 cell lines with IC₅₀ values 2.0-fold lower than DDP.

Key words: indolo[b]tetrahydrofuran, imidazolium salts, hybrid compound, cytotoxic activity

Cite this article

Liu Zhengfen, Zhang Chaobo, Duan Shengzu, Liu Yang, Chen Wen, Li Yan, Zhang Hongbin, Yang Xiaodong. Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts[J]. Chin. J. Org. Chem., 2017, 37(6): 1506-1515.

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吲哚并四氢呋喃-咪唑盐杂合物的合成及细胞毒活性研究

Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts

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