One-pot reaction to obtain N,N'-disubstituted guanidines of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine scaffold as human A3 adenosine receptor antagonists

J Med Chem. 2015 Jul 9;58(13):5355-60. doi: 10.1021/acs.jmedchem.5b00551. Epub 2015 Jun 17.


In this paper we describe an extension SAR study of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine nucleus as A3AR antagonist. Our initial aim was to replace the phenylcarbamoyl moiety at the 5 position of PTP nucleus with a thiourea functionality to evaluate the contribution of new structural modification against the A3AR. The synthesized 12-25 were not characterized by the predicted side chain but by a 1,3-disubstituted guanidine and are shown to be interesting A3AR antagonists.

MeSH terms

  • Animals
  • Binding, Competitive
  • CHO Cells
  • Cricetulus
  • Cyclic AMP / metabolism
  • Drug Design*
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Purinergic P1 Receptor Antagonists / chemistry*
  • Purinergic P1 Receptor Antagonists / pharmacology*
  • Pyrazoles / chemistry*
  • Pyrimidines / chemistry*
  • Radioligand Assay
  • Receptor, Adenosine A3 / chemistry*
  • Structure-Activity Relationship


  • Purinergic P1 Receptor Antagonists
  • Pyrazoles
  • Pyrimidines
  • Receptor, Adenosine A3
  • Cyclic AMP