8-Substituted-9-deazaxanthines as adenosine receptor ligands: design, synthesis and structure-affinity relationships at A2B

Eur J Med Chem. 2004 Oct;39(10):879-87. doi: 10.1016/j.ejmech.2004.07.008.

Abstract

A number of 8-substituted-9-deazaxanthine derivatives (1,3-dialkyl-6-substituted-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-diones) were prepared and tested for their antagonistic activity at the recombinant human adenosine receptors, in particular at the A(2B) and A(2A) receptor subtypes. Compounds endowed with micromolar to nanomolar binding affinities, but with poor A(2B)/A(2A) selectivity, were obtained. Preliminary quantitative structure-affinity relationships suggested that the binding potency at the A(2B) receptor is mainly modulated by the electronic and lipophilic properties of the ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine A2 Receptor Antagonists
  • Animals
  • CHO Cells
  • Cell Line
  • Cricetinae
  • Humans
  • Ligands
  • Protein Binding / physiology
  • Receptor, Adenosine A2B / metabolism*
  • Structure-Activity Relationship
  • Xanthines / chemical synthesis*
  • Xanthines / metabolism*

Substances

  • Adenosine A2 Receptor Antagonists
  • Ligands
  • Receptor, Adenosine A2B
  • Xanthines