A series of ligands displaying a remarkable agonistic-antagonistic profile at the adenosine A1 receptor

J Med Chem. 2005 Mar 24;48(6):2045-53. doi: 10.1021/jm049597+.

Abstract

Adenosine receptor agonists are usually variations of the natural ligand, adenosine. The ribose moiety in the ligand has previously been shown to be of great importance for the agonistic effects of the compound. In this paper, we present a series of nonadenosine ligands selective for the adenosine A(1) receptor with an extraordinary pharmacological profile. 2-Amino-4-benzo[1,3]dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile (70, LUF 5853) shows full agonistic behavior comparable with the reference compound CPA, while also displaying comparable receptor binding affinity (K(i) = 11 nM). In contrast, compound 58 (2-amino-4-(3-trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5948) has a binding affinity of 14 nM and acts as an inverse agonist. Also present within this same series are compounds that show neutral antagonism of the adenosine A(1) receptor, for example compound 65 (2-amino-4-(4-difluoromethoxyphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5826).

MeSH terms

  • Adenosine A1 Receptor Agonists*
  • Adenosine A1 Receptor Antagonists*
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / chemistry
  • Aminopyridines / pharmacology
  • Animals
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Cyclic AMP / biosynthesis
  • Dioxoles / chemical synthesis*
  • Dioxoles / chemistry
  • Dioxoles / pharmacology
  • Ligands
  • Models, Molecular
  • Radioligand Assay
  • Structure-Activity Relationship

Substances

  • 2-amino-4-(3-trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile
  • 2-amino-4-benzo(1,3)dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile
  • Adenosine A1 Receptor Agonists
  • Adenosine A1 Receptor Antagonists
  • Aminopyridines
  • Dioxoles
  • Ligands
  • Cyclic AMP