Journal of Medicinal Chemistry p. 239 - 242 (1985)
Update date:2022-08-04
Topics:
Pellicciari, Roberto
Cecchetti, Sergio
Natalini, Benedetto
Roda, Aldo
Grigolo, Brunella
Fini, Adamo
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.
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