Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity.
Publication
, Journal Article
McKittrick, BA; Ma, K; Huie, K; Yumibe, N; Davis, H; Clader, JW; Czarniecki, M; McPhail, AT
Published in: Journal of medicinal chemistry
February 1998
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.
Duke Scholars
Altmetric Attention Stats
Dimensions Citation Stats
Published In
Journal of medicinal chemistry
DOI
EISSN
1520-4804
ISSN
0022-2623
Publication Date
February 1998
Volume
41
Issue
5
Start / End Page
752 / 759
Related Subject Headings
- Structure-Activity Relationship
- Stereoisomerism
- Molecular Structure
- Medicinal & Biomolecular Chemistry
- Male
- Macaca fascicularis
- Intestinal Absorption
- Cholesterol
- Bile
- Azetidines
Citation
APA
Chicago
ICMJE
MLA
NLM
McKittrick, B. A., Ma, K., Huie, K., Yumibe, N., Davis, H., Clader, J. W., … McPhail, A. T. (1998). Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity. Journal of Medicinal Chemistry, 41(5), 752–759. https://doi.org/10.1021/jm970676d
McKittrick, B. A., K. Ma, K. Huie, N. Yumibe, H. Davis, J. W. Clader, M. Czarniecki, and A. T. McPhail. “Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity.” Journal of Medicinal Chemistry 41, no. 5 (February 1998): 752–59. https://doi.org/10.1021/jm970676d.
McKittrick BA, Ma K, Huie K, Yumibe N, Davis H, Clader JW, et al. Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity. Journal of medicinal chemistry. 1998 Feb;41(5):752–9.
McKittrick, B. A., et al. “Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity.” Journal of Medicinal Chemistry, vol. 41, no. 5, Feb. 1998, pp. 752–59. Epmc, doi:10.1021/jm970676d.
McKittrick BA, Ma K, Huie K, Yumibe N, Davis H, Clader JW, Czarniecki M, McPhail AT. Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity. Journal of medicinal chemistry. 1998 Feb;41(5):752–759.
Published In
Journal of medicinal chemistry
DOI
EISSN
1520-4804
ISSN
0022-2623
Publication Date
February 1998
Volume
41
Issue
5
Start / End Page
752 / 759
Related Subject Headings
- Structure-Activity Relationship
- Stereoisomerism
- Molecular Structure
- Medicinal & Biomolecular Chemistry
- Male
- Macaca fascicularis
- Intestinal Absorption
- Cholesterol
- Bile
- Azetidines