Discovery of the first nonpeptide agonist of the GPR14/urotensin-II receptor: 3-(4-chlorophenyl)-3-(2- (dimethylamino)ethyl)isochroman-1-one (AC-7954)

J Med Chem. 2002 Nov 7;45(23):4950-3. doi: 10.1021/jm025551+.

Abstract

A functional cell-based screen identified 3-(4-chlorophenyl)-3-(2-(dimethylamino)ethyl)isochroman-1-one hydrochloride (AC-7954, 1) as a nonpeptidic agonist of the urotensin-II receptor. Racemic 1 had an EC50 of 300 nM at the human UII receptor and was highly selective. Testing of the enantiopure (+)- and (-)- 1 revealed that the UII receptor activity of racemic 1 resides primarily in (+)-1. Being a selective nonpeptidic druglike UII receptor agonist, (+)-1 will be useful as a pharmacological research tool and a potential drug lead.

MeSH terms

  • Animals
  • Chromans / chemistry*
  • Chromans / pharmacology
  • Combinatorial Chemistry Techniques
  • Humans
  • Mice
  • Rats
  • Receptors, Cell Surface / agonists*
  • Receptors, G-Protein-Coupled*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 3-(4-chlorophenyl)-3-(2-(dimethylamino)ethyl)isochroman-1-one
  • Chromans
  • Receptors, Cell Surface
  • Receptors, G-Protein-Coupled
  • UTS2R protein, human