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

doi:10.6023/cjoc201909042

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

胡椒基咪唑盐类化合物的合成及生物活性研究

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

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 E-mail:xdyang@ynu.edu.cn;zhanghb@ynu.edu.cn
基金资助:
长江学者和创新团队发展计划（No.IRT17R94）、国家自然科学基金（Nos.21662043，21572197，U1402227）、云南省高校科技创新团队支持计划资助项目.

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

Liu Zhengfen^a, Zi Yujin^a, Zhang Linlin^a, Fang Yongsheng^a, Shen Yanzhen^a, Li Yan^b, Yang Xiaodong^a, Zhang Hongbin^a

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.

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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.

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胡椒基咪唑盐类化合物的合成及生物活性研究

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

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