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



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   

  1. 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;
  • 基金资助:


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

Liu Zhengfena, Zhang Chaoboa, Duan Shengzua, Liu Yanga, Chen Wena, Li Yanb, Zhang Hongbina, Yang Xiaodonga   

  1. 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;
  • 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).

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