Synthesis and biological evaluation of novel C-4 aziridine-bearing paclitaxel (taxol) analogs

J Med Chem. 1995 Jun 9;38(12):2263-7. doi: 10.1021/jm00012a029.

Abstract

Three novel C-4 aziridine-bearing paclitaxel analogs, 3-5, have been synthesized during the course of our continuing effort at C-4 modification. The key step in the synthesis is the aziridine ring formation at the C-4 position via an intramolecular Mitsunobu reaction. The syntheses and the biological evaluation of these C-4 aziridine-containing derivatives are herein discussed.

MeSH terms

  • Aziridines / chemistry*
  • Paclitaxel / analogs & derivatives*
  • Paclitaxel / chemical synthesis
  • Paclitaxel / pharmacology
  • Structure-Activity Relationship
  • Tubulin / chemistry

Substances

  • Aziridines
  • Tubulin
  • aziridine
  • Paclitaxel