Synthesis of [1,2,4]triazolo[1,5-a]pyrazines as adenosine A2A receptor antagonists

Bioorg Med Chem Lett. 2005 Nov 1;15(21):4809-13. doi: 10.1016/j.bmcl.2005.07.052.

Abstract

Potent and selective antagonists of the adenosine A2A receptor often contain a nitrogen-rich fused-ring heterocyclic core. Replacement of the core with an isomeric ring system has previously been shown to improve target affinity, selectivity, and in vivo activity. This paper describes the preparation, by a novel route, of A2A receptor antagonists containing the [1,2,4]triazolo[1,5-a]pyrazine nucleus, which is isomeric with the [1,2,4]triazolo[1,5-c]pyrimidine core of a series of known A2A antagonists with in vivo activity in animal models of Parkinson's disease.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Animals
  • Brain / ultrastructure
  • Cell Membrane / chemistry
  • Cell Membrane / metabolism
  • Disease Models, Animal
  • Parkinson Disease / drug therapy
  • Pyrazines / chemical synthesis*
  • Pyrazines / pharmacology
  • Radioligand Assay
  • Rats
  • Structure-Activity Relationship

Substances

  • Adenosine A2 Receptor Antagonists
  • Pyrazines