Sugar-substituted 2-azetidinone cholesterol absorption inhibitors: enhanced potency by modification of the sugar.
A glucuronide conjugate of the potent 2-azetidinone cholesterol absorption inhibitor Sch 58235 was synthesized to confirm the structure of a metabolite isolated from in vivo sources. A series of 2-azetidinone glycosides was prepared via Schmidt trichloroimidate methodology. Enhanced cholesterol absorption inhibition was achieved by modification of the sugar moiety.
Vaccaro
W D
WD
Schering-Plough Research Institute, Kenilworth, New Jersey 07033-0539, USA.
Davis
H R
HR
D000818:Animals; D000924:Anticholesteremic Agents / Q000737:chemistry* / Q000494:pharmacology*; D001384:Azetidines / Q000737:chemistry* / Q000494:pharmacology*; D002241:Carbohydrates / Q000737:chemistry*; D002784:Cholesterol / Q000097:blood / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D006224:Cricetinae; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013329:Structure-Activity Relationship
C116379:2-azetidinone; D000924:Anticholesteremic Agents; D001384:Azetidines; D002241:Carbohydrates; D002784:Cholesterol