3α,7β-Dihydroxy-22,23-methylene-5β-cholan-24-oic acid (5), a side-chain cyclopropyl analogue of ursodeoxycholic acid (1b), has been prepared by the cyclopropanation of 3α,7β-diacetoxy-24-nor-5β-chol-22-ene (2) with ethyl diazoacetate, followed by saponification of the resulting cyclopropyl ester (3). The new bile acid presents similar properties to 1b in water. The sodium salt self-aggregates to form micelles at a concentration of 15.5 mM. The cyclopropane ring does not modify the pKa with respect to compound 1b. Cyclopropyl acid 5 is taken up efficiently by rat liver and promptly secreted into bile. It is partially (70%) conjugated with taurine. The bile flow and bile acids and phospholipids secretion are stimulated by 5, while the cholesterol secretion is stimulated by 5 to a lesser extent.
|Number of pages||4|
|Journal||Journal of Medicinal Chemistry|
|Publication status||Published - 1984|
ASJC Scopus subject areas
- Organic Chemistry