N6-1,3-diphenylurea derivatives of 2-phenyl-9-benzyladenines and 8-azaadenines: synthesis and biological evaluation as allosteric modulators of A2A adenosine receptors

Eur J Med Chem. 2008 Aug;43(8):1639-47. doi: 10.1016/j.ejmech.2007.10.021. Epub 2007 Oct 24.

Abstract

Some 1-[4-(9-benzyl-2-phenyl-9H-purin-6-ylamino)-phenyl]-3-phenyl-urea derivatives and some 1-[4-(9-benzyl-2-phenyl-9H-8-azapurin-6-ylamino)-phenyl]-3-phenyl-urea derivatives were synthesised and evaluated for their interaction with adenosine receptors. It was found that some of these compounds can act as positive enhancers of agonist and antagonist radioligands for the A(2A) adenosine receptors. This evidence was also strengthened by functional data. Other compounds can act as negative modulators. Furthermore these compounds show inhibitory properties for A(1) and A(3) adenosine receptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemical synthesis
  • Adenine / chemistry
  • Adenine / pharmacology
  • Adenosine A2 Receptor Antagonists*
  • Allosteric Regulation / drug effects
  • Animals
  • Kinetics
  • Male
  • Molecular Structure
  • Phenol / chemistry*
  • Rats
  • Rats, Wistar
  • Receptors, Adenosine A2 / metabolism
  • Structure-Activity Relationship
  • Urea / chemistry*

Substances

  • Adenosine A2 Receptor Antagonists
  • Receptors, Adenosine A2
  • Phenol
  • 9-benzyladenine
  • Urea
  • Adenine
  • 8-azaadenine