有机化学 ›› 2009, Vol. 29 ›› Issue (06): 971-974. 上一篇    下一篇

研究简报

一种具有抗肿瘤活性胆酸衍生物的合成新方法

崔建国*; 黄立梁; 黄燕敏; 范建春   

  1. (广西师范学院化学与生命科学学院 南宁 530001)
  • 收稿日期:2008-07-23 修回日期:2008-11-29 发布日期:2009-06-20
  • 通讯作者: 崔建国

A Facile Synthesis of a Cholic Acid Derivative with Anticancer Activity

Cui, Jianguo*; Huang, Liliang; Huang, Yanmin; Fan, Jianchun   

  1. (College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001)
  • Received:2008-07-23 Revised:2008-11-29 Published:2009-06-20
  • Contact: Cui, Jianguo

以胆酸为原料, 使之与甲醇反应, 得到胆酸甲酯(2). 2采用PCC(氯铬酸吡啶)氧化得到脱氢胆酸甲酯(3), 3在CoCl2存在的条件下通过NaBH4的化学选择性还原得到7α-羟基-3,12-二氧代胆酸甲酯(4). 对4的抗肿瘤活性试验表明该化合物对Sk-Hep-1(肝癌)和H-292(肺癌)细胞株具有中等程度的细胞毒性.

关键词: 胆酸, 7α-羟基-3,12-二氧代胆甾-24-酸甲酯, 细胞毒性, 甾体

Cholic acid (1) was transformed into methyl cholic acid (2) by esterification with methanol. Then, 2 was oxidized with pyridinium chlorochromate (PCC) to form methyl dehydrocholic acid (3). Selective reduction of 3 by NaBH4 in the presence of CoCl2 gave methyl 7α-hydroxy-3,12-dioxocholan-24-oic acid (4). The structure of 4 was elucidated by IR, NMR and MS techniques. The cytotoxicity of 4 against some tumor cells was investigated, showing that 4 has antiproliferative activity toward sk-Hep-1 (human liver carcinoma cell line) and H-292 (human lung carcinoma cell line).

Key words: cholic acid, methyl 7α-hydroxy-3,12-dioxocholan-24-oic acid, cytotoxicity, sterol