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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 3: 669 - 678

DOI: https://doi.org/10.6023/cjoc201909042

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

  • Liu Zhengfen ,
  • Zi Yujin ,
  • Zhang Linlin ,
  • Fang Yongsheng ,
  • Shen Yanzhen ,
  • Li Yan ,
  • Yang Xiaodong ,
  • Zhang Hongbin
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  • 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 date: 2019-09-30

  Revised date: 2019-10-31

  Online 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.

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Abstract

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

Cite this article

Liu Zhengfen , Zi Yujin , Zhang Linlin , Fang Yongsheng , Shen Yanzhen , Li Yan , Yang Xiaodong , Zhang Hongbin . Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Piperonyl and Imidazolium Salts[J]. Chinese Journal of Organic Chemistry, 2020 , 40(3) : 669 -678 . DOI: 10.6023/cjoc201909042

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