Synthesis and biological activity of novel epothilone aziridines

Citation
A. Regueiro-ren et al., Synthesis and biological activity of novel epothilone aziridines, ORG LETT, 3(17), 2001, pp. 2693-2696
Citations number
32
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
1523-7060 → ACNP
Volume
3
Issue
17
Year of publication
2001
Pages
2693 - 2696
Database
ISI
SICI code
1523-7060(20010823)3:17<2693:SABAON>2.0.ZU;2-B
Abstract
[GRAPHICS] A series of 12 alpha ,13 alpha -aziridinyl epothilone derivatives were synt hesized in an efficient manner from epothilone A. The final semisynthetic r oute involves a formal double-inversion of stereochemistry at both the C12 and C13 positions. All aziridine analogues were tested for effects on tubul in binding polymerization and cytotoxicity. The results indicate that the a ziridine moiety is a viable isosteric replacement for the epoxide in the ca se of epothilones.