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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (08): 1450-1458.DOI: 10.6023/cjoc201204018 上一篇    下一篇

研究论文

藤黄酸衍生物的合成及抗肿瘤活性研究

张生烈a,b, 李乾a,b, 张磊a,b, 孙昊鹏a,b, 尤启冬a,b,c   

  1. a 天然药物活性组分与药效国家重点实验室 中国药科大学 南京 210009;
    b 中国药科大学药物化学教研室 南京 210009;
    c 江苏省肿瘤发生与干预重点实验室 中国药科大学 南京 210009
  • 收稿日期:2012-04-18 修回日期:2012-05-09 发布日期:2012-05-11
  • 通讯作者: 孙昊鹏, 尤启冬 E-mail:youqidong@gmail.com;sunhaopeng@163.com
  • 基金资助:

    国家自然科学基金(No. 90713038)和重大新药创制科技重大专项(No. 2009ZX09501-003)资助项目.

Synthesis and Bioevaluation of Gambogic Acid Derivatives as Antitumor Agents

Zhang Shengliea,b, Li Qiana,b, Zhang Leia,b, Sun Haopenga,b, You Qidonga,b,c   

  1. a State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009;
    b Department of Medicinal Chemstry, China Pharmaceutical University, Nanjing 210009;
    c Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing 210009
  • Received:2012-04-18 Revised:2012-05-09 Published:2012-05-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 90713038) and the National Key Program for New Drug Development (No. 2009ZX09501-003).

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被引次数

8 | 4

以藤黄酸为原料, 经过C-32位选择性环氧化、高碘酸氧化、甲基化、Jones氧化、不同条件的酯化、酰胺化等反应步骤, 合成了17个藤黄酸衍生物. 所有目标化合物的结构均通过核磁共振谱、红外光谱和质谱证实, 并采用MTT比色法对所合成的目标化合物进行了体外抗肿瘤细胞生物活性测试. 结果表明, 化合物5, 7, 8, 13对人肝癌细胞(HepG2)、人结肠癌细胞(HCT-116)的增殖抑制活性显著强于藤黄酸.

关键词: 藤黄酸, 衍生物, 合成, 抗肿瘤, 生物活性

Seventeen new compounds were synthesized from gambogic acid (GA) with the structural modification of C-32. The reaction steps included selective epoxidation, periodate oxidation, methylation, Jones oxidation, different conditions of esterification, amidation, etc. The structures of target compounds were confirmed by NMR, IR and MS/ESI techniques. Their antitumor activities were evaluated in vitro by MTT assay. The results showed that compounds 5, 7, 8 and 13 were more potent than GA to human hepatoma cells (HepG2) and colon carcinoma cells (HCT-116).

Key words: gambogic acid, derivative, synthesis, antitumor, biological activity