Antagonists of the human adenosine A2A receptor. Part 1: Discovery and synthesis of thieno[3,2-d]pyrimidine-4-methanone derivatives

Bioorg Med Chem Lett. 2008 May 1;18(9):2916-9. doi: 10.1016/j.bmcl.2008.03.075. Epub 2008 Mar 30.

Abstract

The (-)-(11R,2'S)-enantiomer of the antimalarial drug mefloquine has been found to be a reasonably potent and moderately selective adenosine A(2A) receptor antagonist. Further investigation of this compound has led to the discovery of a series of keto-aryl thieno[3,2-d]pyrimidine derivatives, which are potent and selective antagonists of the adenosine A(2A) receptor. These derivatives show selectivity against the A(1) receptor. Furthermore, some of these compounds have been shown to have in vivo activity in a commonly used model, suggesting the potential for the treatment of Parkinson's disease.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Antimalarials / chemical synthesis
  • Antimalarials / therapeutic use*
  • Antiparkinson Agents / chemical synthesis
  • Antiparkinson Agents / therapeutic use*
  • Humans
  • Models, Chemical
  • Parkinsonian Disorders / drug therapy*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / therapeutic use*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Adenosine A2 Receptor Antagonists
  • Antimalarials
  • Antiparkinson Agents
  • Pyrimidines
  • thieno(3,2-d)pyrimidine-4-methanone