Heterocyclic ring scaffolds as small-molecule cholesterol absorption inhibitors.
Enantio- and diastereoselective syntheses of a substituted oxazolidinone, isoxazoline and pyrazoline as beta-lactam surrogates are described. The substituted heterocycles were designed to incorporate side chains closely resembling those found in the beta-lactam cholesterol absorption inhibitor ezetimibe (1). Additionally, the in vitro inhibitory efficacy of the novel compounds as cholesterol absorption inhibitors is reported using a brush border membrane vesicle assay.
Ritter
Tobias
T
Laboratorium für Organische Chemie, ETH-Hönggerberg, CH-8093 Zürich, Switzerland.
Kvaernø
Lisbet
L
Werder
Moritz
M
Hauser
Helmut
H
Carreira
Erick M
EM
D000924:Anticholesteremic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001384:Azetidines / Q000494:pharmacology; D000069438:Ezetimibe; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007555:Isoxazoles / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry
D000924:Anticholesteremic Agents; D001384:Azetidines; D006571:Heterocyclic Compounds; D007555:Isoxazoles; D023303:Oxazolidinones; D011720:Pyrazoles; D047090:beta-Lactams; D000069438:Ezetimibe