Abstract |
The absolute configuration of strongylophorine-26 (1) was determined to be 4S, 5R, 8R, 9S, 10S, 13S, 14S by single-crystal X-ray diffraction analysis of the derivative 7 prepared from the co-occurring metabolite strongylophorine-8 (4) and chemical interconversion to the bislactone 8. Synthetic analogues (+)- and (-)-3 have been prepared in order to explore the structure-activity relationship for the anti-invasion pharmacophore of stronglylophorine-26. These studies revealed the unanticipated importance of the A ring lactone moiety for the anti-invasion activity of 1.
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Authors | Kaoru Warabi, Brian O Patrick, Pamela Austin, Calvin D Roskelley, Michel Roberge, Raymond J Andersen |
Journal | Journal of natural products
(J Nat Prod)
Vol. 70
Issue 5
Pg. 736-40
(May 2007)
ISSN: 0163-3864 [Print] United States |
PMID | 17407351
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Antineoplastic Agents
- Diterpenes
- strongylophorine-26
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Topics |
- Antineoplastic Agents
(chemical synthesis, chemistry, pharmacology)
- Diterpenes
(chemical synthesis, chemistry, pharmacology)
- Drug Screening Assays, Antitumor
- Molecular Structure
- Stereoisomerism
- Structure-Activity Relationship
- X-Ray Diffraction
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