New pyrrolopyrimidin-6-yl benzenesulfonamides: potent A2B adenosine receptor antagonists

Bioorg Med Chem Lett. 2006 Jul 15;16(14):3642-5. doi: 10.1016/j.bmcl.2006.04.074. Epub 2006 May 11.

Abstract

A new series of 4-(1,3-dialkyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamides has been identified as potent A2B adenosine receptor antagonists. The products have been evaluated for their binding affinities for the human A2B, A1 and A3 adenosine receptors. 6-(4-{[4-(4-Bromobenzyl)piperazin-1-yl]sulfonyl}phenyl)-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (16) showed a high affinity for the A2B adenosine receptor (IC50=1 nM) and selectivity (A1: 183x; A3: 12660x). Synthesis and SAR of this novel class of compounds showing improved absorption properties is presented herein.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Binding, Competitive
  • Drug Design
  • Humans
  • Inhibitory Concentration 50
  • Pyrimidinones / chemical synthesis*
  • Pyrimidinones / pharmacology*
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology*

Substances

  • Adenosine A2 Receptor Antagonists
  • Pyrimidinones
  • Sulfonamides