Deletion of the oxetane ring in docetaxel analogues: synthesis and biological evaluation

Org Lett. 2003 Dec 25;5(26):5031-4. doi: 10.1021/ol036043c.

Abstract

Two new docetaxel analogues have been prepared starting from 10-deacetylbaccatin III. Both derivatives lack the oxetane D-ring but possess the 4alpha-acetoxy group, which is important for biological activity. The influence of a more or less constrained C-ring was evaluated by adding, or not adding, a double bond in this ring. Both compounds were found to be equally less active than docetaxel in biological assays. [reaction: see text]

MeSH terms

  • Acetylation
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Docetaxel
  • Ethers, Cyclic / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Stereoisomerism
  • Structure-Activity Relationship
  • Taxoids / chemical synthesis*

Substances

  • Antineoplastic Agents, Phytogenic
  • Ethers, Cyclic
  • Indicators and Reagents
  • Taxoids
  • Docetaxel
  • oxetane