Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid

doi:10.6023/cjoc201510034

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1080-1087.DOI: 10.6023/cjoc201510034 Previous Articles Next Articles

ARTICLE

熊果酸A环衍生物的合成及抗肿瘤活性研究

孟艳秋, 曹佳, 汤义, 鹿学宇, 刘立伟

沈阳化工大学制药工程教研室沈阳 110142

收稿日期:2015-10-28 修回日期:2015-12-16 发布日期:2016-01-04
通讯作者: 孟艳秋 E-mail:mengyanqiu@hotmail.com
基金资助:
国家自然科学基金(No.21372156)、辽宁省教育厅高等学校优秀人才支持计划(No.LR2013017)和沈阳市科学技术计划(No.F16-230-6-00)资助项目.

Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid

Meng Yanqiu, Cao Jia, Tang Yi, Lu Xueyu, Liu Liwei

Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142

Received:2015-10-28 Revised:2015-12-16 Published:2016-01-04
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372156), the Education Department of Higher School Outstanding Talent Support Program in Liaoning Province (No. LR2013017) and the Science and Technology Project in Shenyang (No. F 16-230-6-00) .

1. Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid.PDF(18236KB)

Abstract

Ten derivatives were successfully synthesized by the introduction of nitrogen-and oxygen-containing heterocyclic compounds at ring A and the modification of the amidation at C(28) position in the natural product ursolic acid, which structures were characterized by ¹H NMR, ¹³C NMR, MS and elemental analysis. Their anti-tumor activities against KB and SGC7901 cells in vitro were evaluated by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. These results indicated that all of derivatives can inhibit cell proliferation of KB and SGC7901 cells better than ursolic acid (UA), and UA_4-1 (IC₅₀=0. 289 μmol/L) and UA_4-2 (IC₅₀=0. 04 μmol/L) were also found to have especially more potent inhibitory activity on SGC7901 tumor cells than that of the positive control drug gefitinib (IC₅₀=1. 03 μmol/L).

Key words: pentacyclic trierpenoid, ursolic acid, anti-tumor activity

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Meng Yanqiu, Cao Jia, Tang Yi, Lu Xueyu, Liu Liwei. Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid[J]. Chin. J. Org. Chem., 2016, 36(5): 1080-1087.

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熊果酸A环衍生物的合成及抗肿瘤活性研究

Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid

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