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Synthesis and anti-tubulin activity of a 3'-(4-azidophenyl)-3'-dephenylpaclitaxel photoaffinity probe.

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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Spletstoser JT,Flaherty PT,Himes RH,Georg GI

doi

10.1021/jm030581d

keywords:

subject

Has Abstract

pub_date

2004-12-16 00:00:00

pages

6459-65

issue

26

eissn

0022-2623

issn

1520-4804

journal_volume

47

pub_type

杂志文章

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