Selective, high affinity A(2B) adenosine receptor antagonists: N-1 monosubstituted 8-(pyrazol-4-yl)xanthines

Bioorg Med Chem Lett. 2008 Feb 15;18(4):1397-401. doi: 10.1016/j.bmcl.2008.01.008. Epub 2008 Jan 8.

Abstract

A series of N-1 monosubstituted 8-pyrazolyl xanthines have been synthesized and evaluated for their affinity for the adenosine receptors (AdoRs). We have discovered two compounds 18 (CVT-7124) and 28 (CVT-6694) that display good affinity for the A(2B) AdoR (K(i)=6 nM and 7 nM, respectively) and greater selectivity for the human A(1), A(2A), and A(3) AdoRs (>1000-, >830-, and >1500-fold; >850-, >700-, and >1280-fold, respectively). CVT-6694 has been shown to block the release of interleukin-6 and monocyte chemotactic protein-1 from bronchial smooth muscle cells (BSMC), a process believed to be promoted by activation of A(2B) AdoR.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Animals
  • Binding, Competitive
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Humans
  • Kinetics
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Receptor, Adenosine A2B / metabolism
  • Substrate Specificity
  • Uracil / analogs & derivatives
  • Uracil / chemistry
  • Xanthines / chemical synthesis
  • Xanthines / chemistry
  • Xanthines / pharmacology*

Substances

  • Adenosine A2 Receptor Antagonists
  • Pyrazoles
  • Receptor, Adenosine A2B
  • Xanthines
  • Uracil