Bile acids with a cyclopropyl-containing side chain. 1. Preparation and properties of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid

Roberto Pellicciari, Sergio Cecchetti, Benedetto Natalini, Aldo Roda, Brunella Grigolo, Adamo Fini

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)746-749
Number of pages4
JournalJournal of Medicinal Chemistry
Volume27
Issue number6
Publication statusPublished - 1984

ASJC Scopus subject areas

  • Organic Chemistry

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