Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity.

Journal Article (Journal Article)

The C3 phenylpropyl side chain of N-phenylazetidinones related to SCH 56524 was modified by replacing the hydroxymethylene with various isoelectronic or isosteric groups. Modifications at the 3' position led to less-active compounds; however, modifications at the 1' position provided compounds with improved cholesterol absorption inhibitory activity. An enantioselective route for the synthesis of C3 1'-sulfur-substituted azetidinones and the development of structure-activity relationships for this series of compounds are presented.

Full Text

Duke Authors

Cited Authors

  • McKittrick, BA; Ma, K; Huie, K; Yumibe, N; Davis, H; Clader, JW; Czarniecki, M; McPhail, AT

Published Date

  • February 1998

Published In

Volume / Issue

  • 41 / 5

Start / End Page

  • 752 - 759

PubMed ID

  • 9513603

Electronic International Standard Serial Number (EISSN)

  • 1520-4804

International Standard Serial Number (ISSN)

  • 0022-2623

Digital Object Identifier (DOI)

  • 10.1021/jm970676d


  • eng