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

Haibo Ge, Jianmei Wang, Margaret M. Kayser, Richard H. Himes, Gunda I. Georg

Research output: Contribution to journalArticle

2 Scopus citations

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.

Original languageEnglish
Pages (from-to)6165-6167
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number23
DOIs
StatePublished - Dec 1 2008

Keywords

  • Cytotoxicity
  • Kinetic resolution
  • MCF7
  • NCI/ADR RES
  • Paclitaxel analogues
  • Semisynthesis
  • Tubulin assembly

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