A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

被引：18

作者：

He, Xiao-Long ^{[1
]}

Wang, Li-Ting ^{[1
]}

Gu, Xiang-Zhong ^{[2
]}

Xiao, Jie-Xin ^{[1
]}

Qiu, Wen-Wei ^{[1
]}

机构：

[1] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Sch Chem & Chem Engn, Shanghai 200241, Peoples R China

[2] Jiangsu Jiaerke Pharmaceut Grp Co Ltd, Dept Res & Dev, Zhenglu Town 213111, Changzhou, Peoples R China

来源：

STEROIDS | 2018年 / 140卷

关键词：

Ursodeoxycholic acid; Obeticholic acid; Cholic acid; Synthesis; PRIMARY BILIARY-CIRRHOSIS; NONALCOHOLIC FATTY LIVER; DISEASE; STEATOHEPATITIS; THERAPIES; AGONIST; POTENT; NASH;

D O I：

10.1016/j.steroids.2018.10.009

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

引用

页码：173 / 178

页数：6

共 40 条

[1] Biotransformation of methyl cholate by Aspergillus niger [J].