(1-(4-(Naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine: a wingless beta-catenin agonist that increases bone formation rate

J Med Chem. 2009 Nov 26;52(22):6962-5. doi: 10.1021/jm9014197.

Abstract

A high-throughput screening campaign to discover small molecule leads for the treatment of bone disorders concluded with the discovery of a compound with a 2-aminopyrimidine template that targeted the Wnt beta-catenin cellular messaging system. Hit-to-lead in vitro optimization for target activity and molecular properties led to the discovery of (1-(4-(naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine (5, WAY-262611). Compound 5 has excellent pharmacokinetic properties and showed a dose dependent increase in the trabecular bone formation rate in ovariectomized rats following oral administration.

MeSH terms

  • Animals
  • Catalytic Domain
  • Cell Line, Tumor
  • Glycogen Synthase Kinase 3 / antagonists & inhibitors
  • Glycogen Synthase Kinase 3 / chemistry
  • Glycogen Synthase Kinase 3 beta
  • Humans
  • Mice
  • Models, Molecular
  • Osteogenesis / drug effects*
  • Piperidines / administration & dosage
  • Piperidines / pharmacokinetics
  • Piperidines / pharmacology*
  • Pyrimidines / administration & dosage
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / pharmacology*
  • Rats
  • Signal Transduction / drug effects
  • Wnt Proteins / agonists*
  • Wnt Proteins / metabolism
  • beta Catenin / agonists*
  • beta Catenin / metabolism

Substances

  • Piperidines
  • Pyrimidines
  • WAY-262611
  • Wnt Proteins
  • beta Catenin
  • Glycogen Synthase Kinase 3 beta
  • Glycogen Synthase Kinase 3