Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1506-1515. doi: 10.6023/cjoc201610043 shu

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

Corresponding author: Zhang Hongbin, zhanghb@ynu.edu.cn Yang Xiaodong, xdyang@ynu.edu.cn
Received Date: 28 October 2016
Revised Date: 12 January 2017

Fund Project: the National Natural Science Foundation of China 21662043the National Natural Science Foundation of China 21332007the Program for Changjiang Scholars and Innovative Research Team in University IRT13095the Natural Science Foundation of Yunnan Province 2013FA028the National Natural Science Foundation of China 21462049the National Natural Science Foundation of China U1402227

Figures(5)

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.
- indolo[b]tetrahydrofuran,
- imidazolium salts,
- hybrid compound,
- cytotoxic activity
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