Bile acids with cyclopropane-containing side chain. 2. Synthesis and properties of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide

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

Research output: Contribution to journalArticlepeer-review

Abstract

The preparation of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid "cyclopropylog" (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.

Original languageEnglish
Pages (from-to)239-242
Number of pages4
JournalJournal of Medicinal Chemistry
Volume28
Issue number2
Publication statusPublished - 1985

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Bile acids with cyclopropane-containing side chain. 2. Synthesis and properties of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide'. Together they form a unique fingerprint.

Cite this