Synthesis and biological activity of novel epothilone aziridines

Org Lett. 2001 Aug 23;3(17):2693-6. doi: 10.1021/ol016273w.

Abstract

[reaction: see text]. A series of 12alpha,13alpha-aziridinyl epothilone derivatives were synthesized in an efficient manner from epothilone A. The final semisynthetic route involves a formal double-inversion of stereochemistry at both the C12 and C13 positions. All aziridine analogues were tested for effects on tubulin binding polymerization and cytotoxicity. The results indicate that the aziridine moiety is a viable isosteric replacement for the epoxide in the case of epothilones.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Aziridines / pharmacology*
  • Epoxy Compounds / chemistry*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Aziridines
  • Epoxy Compounds