Synthesis and anti-tubulin activity of a 3′-(4-Azidophenyl)-3′- dephenylpaclitaxel photoaffinity probe

Jared T. Spletstoser, Patrick T. Flaherty, Richard H. Himes, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3′-(4-azidophenyl)-3′- dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.

Original languageEnglish (US)
Pages (from-to)6459-6465
Number of pages7
JournalJournal of medicinal chemistry
Volume47
Issue number26
DOIs
StatePublished - Dec 16 2004

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