The preparation of bile acid amides and oxazolines. II. The synthesis of the amides and oxazolines of ursodeoxycholic acid, deoxycholic acid, hyodeoxycholic acid and cholic acid.
Bile acid amides and oxazolines were synthesized by a sequence of steps involving the reaction of the free bile acid with formic acid to yield the formyloxy derivative, preparation of the formyloxy acid chloride, condensation of the acid chloride with 2-amino-2-methyl-1-propanol to give the amide and, finally, cyclization of the amide with thionyl chloride to give the oxazoline. The oxazolines were characterized by physical constants, thin layer and gas-liquid chromatography and identified by elemental analysis and gas-liquid chromatography-mass spectrometry. Some of the bile acid oxazoline derivatives alter the activity of bacterial 7-dehydroxylases in vitro, and inhibit the growth of certain anaerobic bacteria in pure culture.
D000577:Amides; D001419:Bacteria / Q000201:enzymology; D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000494:pharmacology; D002849:Chromatography, Gas; D008401:Gas Chromatography-Mass Spectrometry; D006913:Hydroxysteroid Dehydrogenases; D007202:Indicators and Reagents; D010080:Oxazoles; D010088:Oxidoreductases; D013250:Steroid Hydroxylases / Q000378:metabolism; D013329:Structure-Activity Relationship
D000577:Amides; D001647:Bile Acids and Salts; D007202:Indicators and Reagents; D010080:Oxazoles; D010088:Oxidoreductases; D006913:Hydroxysteroid Dehydrogenases; C025376:7 alpha-hydroxysteroid dehydrogenase; D013250:Steroid Hydroxylases