Bile acids with cyclopropane-containing side chain. 2. Synthesis and properties of 3 alpha,7 beta-dihydroxy-22,23-methylene-5 beta-cholan-24-oic acid (2-sulfoethyl)amide.
The preparation of 3 alpha,7 beta-dihydroxy-22,23-methylene-5 beta-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.
D000693:Anaerobiosis; D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000494:pharmacology; D002793:Cholic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D005243:Feces / Q000032:analysis; D006801:Humans; D007422:Intestines / Q000382:microbiology; D013329:Structure-Activity Relationship
D001647:Bile Acids and Salts; D002793:Cholic Acids; C044511:3,7-dihydroxy-22,23-methylene-cholan-24-oic acid (2-sulfoethyl)amide