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 journalArticle

21 Citations (Scopus)

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

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Bile Acids and Salts
Amides
Ursodeoxycholic Acid
Acids
Taurine
Bacteria
Degradation
cyclopropane
3,7-dihydroxy-22,23-methylene-cholan-24-oic acid (2-sulfoethyl)amide
EEDQ

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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

In: Journal of Medicinal Chemistry, Vol. 28, No. 2, 1985, p. 239-242.

Research output: Contribution to journalArticle

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AU - Cecchetti, Sergio

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AU - Roda, Aldo

AU - Grigolo, Brunella

AU - Fini, Adamo

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