Novel synthesis of 8-deaza-5,6,7,8-tetrahydroaminopterin analogues via an aziridine intermediate

Molecules. 2012 May 10;17(5):5604-14. doi: 10.3390/molecules17055604.

Abstract

An efficient method for the construction of the tetrahydrofolate skeleton is described. Starting from pterin analogues and aromatic amines, 8-deaza-5,6,7,8-tetrahydroaminopterin derivatives and the heterocyclic benzoyl isosteres were synthesized via a novel aziridine intermediate. Following this method, the byproducts of carbon-nitrogen bond hydrogenolysis in traditional synthetic strategy can be completely avoided.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminopterin / analogs & derivatives
  • Aminopterin / chemical synthesis*
  • Aziridines / chemistry*
  • Carbon / chemistry
  • Hydrogenation
  • Magnetic Resonance Spectroscopy
  • Nitrogen / chemistry
  • Tetrahydrofolates / chemistry

Substances

  • Aziridines
  • Tetrahydrofolates
  • 5,6,7,8-tetrahydrofolic acid
  • aziridine
  • Carbon
  • Aminopterin
  • Nitrogen