Heterocyclic ring scaffolds as small-molecule cholesterol absorption inhibitors

Abstract

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.