Synthesis, structure proof, and biological activity of epothilone cyclopropanes

Citation
J. Johnson et al., Synthesis, structure proof, and biological activity of epothilone cyclopropanes, ORG LETT, 2(11), 2000, pp. 1537-1540
Citations number
32
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
1523-7060 → ACNP
Volume
2
Issue
11
Year of publication
2000
Pages
1537 - 1540
Database
ISI
SICI code
1523-7060(20000601)2:11<1537:SSPABA>2.0.ZU;2-6
Abstract
[GRAPHICS] A semisynthetic route to epothilone cyclopropanes from epothilones A and B is described. Of significance, the deoxygenation of the 12,13- epoxide to g ive the corresponding olefin was achieved with high efficiency. The title c ompounds (8, 9) were active in both tubulin polymerization and cytotoxicity assays, which is in direct contrast to a previously published report. Thes e results provide further evidence that the role of the 12,13 epoxide of ep othilones is largely conformational and argue against some of the current p harmacophore models.