Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives

doi:10.6023/cjoc202003037

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2051-2061.DOI: 10.6023/cjoc202003037 Previous Articles Next Articles

C-乙烯基鼠李糖苷衍生物的合成及细胞毒活性探究

吉玉, 姚辉, 柳乂, 黄年玉, 刘明国

三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室湖北宜昌 443002

收稿日期:2020-03-14 修回日期:2020-04-19 发布日期:2020-04-23
通讯作者: 黄年玉, 刘明国 E-mail:hny115@126.com;mgliu1966@163.com
基金资助:
国家自然科学基金（No.21602123）及三峡大学青年拔尖人才项目和研究生创新基金（No.SDYC2016121）资助项目.

Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives

Ji Yu, Yao Hui, Liu Yi, Huang Nianyu, Liu Mingguo

Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002

Received:2020-03-14 Revised:2020-04-19 Published:2020-04-23
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21602123), and the Youth Talent Development Foundation and Scientific Foundation from Graduate School of China Three Gorges University (No. SDYC2016121).

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Abstract

A novel gold(I)-catalyzed glycosylation method was described to synthesize C-vinyl-rhamnopyranoside derivatives using stable propargylic carboxylates and 3,4-di-O-acetyl-L-rhamnal as starting materials, based on the tandem intermolecular 1,3-acyloxy migration/Ferrier rearrangement. The C-glycosylation process has been verified by O¹⁸ isotopic labeling experiment, and the absolute configuration of synthesized products was determined by X-ray single crystal diffraction. The cytotoxic activity was investigated by methyl thiazolyl tetrazolium (MTT). It indicates that product 3i has strong inhibitory effect on human gastric cancer cells HGC-27 with IC₅₀ 18.29 μmol·L^-1. The described synthetic method was outstanding with easy-to-operate, high diastereoselectivity, and mild reaction condition.

Key words: Ferrier rearrangement, rhamnopyranoside, cytotoxic activity, diastereoselectivity

Cite this article

Ji Yu, Yao Hui, Liu Yi, Huang Nianyu, Liu Mingguo. Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2051-2061.

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C-乙烯基鼠李糖苷衍生物的合成及细胞毒活性探究

Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives

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