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Bioorg Med Chem Lett. 2008 Dec 1;18(23):6165-7. doi: 10.1016/j.bmcl.2008.10.010. Epub 2008 Oct 7.

Synthesis, tubulin assembly, and antiproliferative activity against MCF7 and NCI/ADR-RES cancer cells of 10-O-acetyl-5'-hydroxybutitaxel.

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1
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA.

Abstract

A highly efficient kinetic resolution of racemic cis-4-(2-tert-butyldimethylsilyloxy-1,1-dimethyl)ethyl-3-tert-butyldimethylsilyloxy-azetidin-2-one with 7-O-triethylsilylbaccatin III was carried out to furnish 10-O-acetyl-5'-hydroxybutitaxel after removal of the silyl protecting groups. The compound was 50% as active as paclitaxel in a tubulin assembly assay and showed significantly decreased activity against MCF7 cell proliferation compared to paclitaxel.

PMID:
18977659
PMCID:
PMC2636847
DOI:
10.1016/j.bmcl.2008.10.010
[Indexed for MEDLINE]
Free PMC Article
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