Design, Synthesis and Anticancer Activity of Shikonin and Alkannin Derivatives with Different Substituents on the Naphthazarin Scaffold

doi:10.1007/s40242-015-4385-y

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (3): 394-400.doi: 10.1007/s40242-015-4385-y

Design, Synthesis and Anticancer Activity of Shikonin and Alkannin Derivatives with Different Substituents on the Naphthazarin Scaffold

ZHANG Xu, CUI Jiahua, ZHOU Wen, LI Shaoshun

School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, P. R. China

收稿日期:2014-10-14 修回日期:2014-12-12 出版日期:2015-06-01 发布日期:2014-12-22
通讯作者: LI Shaoshun E-mail:ssli@sjtu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.81373274) and the State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China (No.CHEMR2012-B08).

Design, Synthesis and Anticancer Activity of Shikonin and Alkannin Derivatives with Different Substituents on the Naphthazarin Scaffold

ZHANG Xu, CUI Jiahua, ZHOU Wen, LI Shaoshun

School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, P. R. China

Received:2014-10-14 Revised:2014-12-12 Online:2015-06-01 Published:2014-12-22
Contact: LI Shaoshun E-mail:ssli@sjtu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.81373274) and the State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China (No.CHEMR2012-B08).

摘要/Abstract

摘要：

Based on the asymmetric reduction of alkannin ketone derivative 4 by diisopinocampheylchloro-borane(DIP-Cl), a series of shikonin and alkannin derivatives was designed, synthesized and their anticancer activities against various kinds of cell lines were evaluated. The in vitro biological experiments demonstrated that compound S-10, a 5,8-O-dimethyl-1,4-dioxime alkannin derivative, not only displayed excellent antiproliferative activity against cancer cells, but also exhibited low toxicity towards normal cells. It could induce HCT-116 cell apoptosis, but had no impact on the cell cycle. The underlying anticancer mechanism of S-10 is most likely different from other shikonin and alkannin derivatives.

关键词: Shikonin and alkannin oxime derivative, Asymmetric reduction, Anticancer, Apoptosis, Cell cycle

Abstract:

Key words: Shikonin and alkannin oxime derivative, Asymmetric reduction, Anticancer, Apoptosis, Cell cycle

ZHANG Xu, CUI Jiahua, ZHOU Wen, LI Shaoshun. Design, Synthesis and Anticancer Activity of Shikonin and Alkannin Derivatives with Different Substituents on the Naphthazarin Scaffold[J]. 高等学校化学研究, 2015, 31(3): 394-400.

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Design, Synthesis and Anticancer Activity of Shikonin and Alkannin Derivatives with Different Substituents on the Naphthazarin Scaffold

Design, Synthesis and Anticancer Activity of Shikonin and Alkannin Derivatives with Different Substituents on the Naphthazarin Scaffold

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