Synthesis of benzo[1,2-d;3,4-d']diimidazole and 1H-pyrazolo[4,3-b]pyridine as putative A2A receptor antagonists

Org Biomol Chem. 2007 Aug 21;5(16):2567-71. doi: 10.1039/b707599e.

Abstract

The synthesis and the binding affinity for the putative adenosine receptor antagonist 6-methyl-7-[1,2,3]triazol-2-yl-1,6-dihydrobenzo[1,2-d;3,4-d']diimidazole (10) and 5-oxazol-2-yl-1H-pyrazolo[4,3-b]pyridin-3-ylamine (16) are reported. The title compounds were prepared from commercially available 1-chloro-2,4-dinitrobenzene (1) and 2-chloro-6-methoxy-3nitropyridine (11), respectively, but proved devoid of affinity for the adenosine A1 and A2A receptors.

MeSH terms

  • Adenosine A1 Receptor Antagonists
  • Adenosine A2 Receptor Antagonists*
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Binding Sites
  • Binding, Competitive
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Oxazoles / pharmacology*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Stereoisomerism
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • 5-oxazol-2-yl-1H-pyrazolo(4,3-b)pyridin-3-ylamine
  • 6-methyl-7-(1,2,3)triazol-2-yl-1,6-dihydrobenzo(1,2-d-3,4-d')diimidazole
  • Adenosine A1 Receptor Antagonists
  • Adenosine A2 Receptor Antagonists
  • Benzimidazoles
  • Oxazoles
  • Pyrazoles
  • Triazoles