Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 669-678.DOI: 10.6023/cjoc201909042 Previous Articles     Next Articles


刘正芬a, 字玉金a, 张琳琳a, 方永晟a, 沈艳珍a, 李艳b, 羊晓东a, 张洪彬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:2019-09-30 修回日期:2019-10-31 发布日期:2020-04-02
  • 通讯作者: 羊晓东, 张洪彬;
  • 基金资助:

Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Piperonyl and Imidazolium Salts

Liu Zhengfena, Zi Yujina, Zhang Linlina, Fang Yongshenga, Shen Yanzhena, Li Yanb, Yang Xiaodonga, Zhang Hongbina   

  1. a Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091;
    b State Key Laboratory for Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650204
  • Received:2019-09-30 Revised:2019-10-31 Published:2020-04-02
  • Supported by:
    Project supported by the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT17R94), the National Natural Science Foundation of China (Nos. 21662043, 21572197, U1402227), and the Innovative Research Team (in Science and Technology) in University of Yunnan Province.

A series of novel hybrid compounds between piperonyl and imidazolium salts were prepared from tryptophol by four steps of reduction, mesylation, 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-((benzo[d] [1,3]dioxol-5-ylmethyl)-3-(2-naphthylmethyl))-5,6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (30) exhibited remarkable inhibitory activity selectively against HL-60, SMMC-7721, A-549, MCF-7 and SW480 cell lines compared with DDP. In particular, the compound was more selective to HL-60 cell lines with IC50 values 7.2-fold lower than DDP. Further studies showed that compound 30 has the effect of inducing SMMC-7721 cell line arrest and cell apoptosis in cell cycle G0/G1.

Key words: piperonyl, imidazolium salts, molecular hybridization, structure-activity relationship, cytotoxic activity