Synthesis of a transition state analogue inhibitor of purine nucleoside phosphorylase via the Mannich reaction

Org Lett. 2003 Oct 2;5(20):3639-40. doi: 10.1021/ol035293q.

Abstract

[reaction: see text] The expeditious convergent synthesis of the potent human purine nucleoside phosphorylase inhibitor DADMe-Immucillin-G (3) was achieved via the Mannich reaction. The Mannich chemistry of a series of deazapurines and amine hydrochlorides was also investigated.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amines / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Purine-Nucleoside Phosphorylase / antagonists & inhibitors*
  • Purines / chemistry
  • Pyrimidinones / chemical synthesis*
  • Pyrimidinones / chemistry
  • Pyrimidinones / pharmacology
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology

Substances

  • Amines
  • Enzyme Inhibitors
  • Purines
  • Pyrimidinones
  • Pyrroles
  • immucillin G
  • Purine-Nucleoside Phosphorylase