3-arylimino-2-indolones are potent and selective galanin GAL3 receptor antagonists

J Med Chem. 2006 Jun 29;49(13):3757-8. doi: 10.1021/jm060001n.

Abstract

A series of 3-imino-2-indolones are the first published, high-affinity antagonists of the galanin GAL3 receptor. One example, 1,3-dihydro-1-phenyl-3-[[3-(trifluoromethyl)phenyl]imino]-2H-indol-2-one (9), was shown to have high affinity for the human GAL3 receptor (Ki=17 nM) and to be highly selective for GAL3 over a broad panel of targets, including GAL1 and GAL2. Compound 9 was also shown to be an antagonist in a human GAL3 receptor functional assay (Kb=29 nM).

MeSH terms

  • Animals
  • Binding, Competitive
  • Brain / metabolism
  • COS Cells
  • Chlorocebus aethiops
  • Cyclic AMP / biosynthesis
  • Humans
  • Imines / chemical synthesis*
  • Imines / pharmacokinetics
  • Imines / pharmacology
  • Indoles / chemical synthesis*
  • Indoles / pharmacokinetics
  • Indoles / pharmacology
  • Ligands
  • Radioligand Assay
  • Rats
  • Receptor, Galanin, Type 1 / drug effects
  • Receptor, Galanin, Type 2 / drug effects
  • Receptor, Galanin, Type 3 / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Imines
  • Indoles
  • Ligands
  • Receptor, Galanin, Type 1
  • Receptor, Galanin, Type 2
  • Receptor, Galanin, Type 3
  • Cyclic AMP
  • 1,3-dihydro-1-phenyl-3-((3-(trifluoromethyl)phenyl)imino)-2H-indol-2-one