Novel Biologically Active Taxol Analogues: Baccatin III 13-(N-(p-chlorobenzoyl)-(2′R,3′S)-3′-phenylisoserinate ) and Baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-chlorophenyl)isoserinate )

Gunda I. Georg, Zacharia S. Cheruvallath, Richard H. Himes, Magdalena R. Mejillano

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

Two novel taxol analogues, baccatin III 13-(N-(p-chlorobenzoyl)-(2′R,3′S)-phenylisoserinate) (2) and baccatin III 13-(N-benzoyl-(2′R,3′S)-3′(p-chlorophenyl)isoserinate) (3) were synthesized from 7-triethylsilyl baccatin III (4) and N-acyl 3-ethoxyethyloxy-4-aryl-2-azetidinones 5 and 6 in two steps and excellent overall yield. Both derivatives demonstrated activity in the microtubule assembly assay and cytotoxicity against B16 melanoma cells comparable to taxol.

Original languageEnglish (US)
Pages (from-to)295-298
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume2
Issue number4
DOIs
StatePublished - 1992

Keywords

  • Taxol analogues
  • cytotoxicity
  • microtubule assembly
  • synthesis
  • β-lactams

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