A Facile Synthesis of a Cholic Acid Derivative with Anticancer Activity

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (06): 971-974. Previous Articles Next Articles

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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

(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

(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

Abstract

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

Cite this article

Cui, Jianguo*; Huang, Liliang; Huang, Yanmin; Fan, Jianchun. A Facile Synthesis of a Cholic Acid Derivative with Anticancer Activity[J]. Chin. J. Org. Chem., 2009, 29(06): 971-974.

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一种具有抗肿瘤活性胆酸衍生物的合成新方法

A Facile Synthesis of a Cholic Acid Derivative with Anticancer Activity

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