2,5-Diaminopyrimidines and 3,5-disubstituted azapurines as inhibitors of glycogen synthase kinase-3 (GSK-3)

Bioorg Med Chem Lett. 2008 Jun 15;18(12):3578-81. doi: 10.1016/j.bmcl.2008.05.001. Epub 2008 May 6.

Abstract

The discovery of two classes of pyrimidine-based inhibitors of GSK-3 is described. Optimization of these series led to inhibitors with IC(50)<10nM and >100-fold selectivity over Aurora A kinase. A proposed binding mode of 21b is presented. One compound (33) of the pyrimidine series showed promising pharmacokinetic parameters.

MeSH terms

  • Administration, Oral
  • Animals
  • Aurora Kinase A
  • Aurora Kinases
  • Binding Sites
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Glycogen Synthase Kinase 3 / antagonists & inhibitors*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Serine-Threonine Kinases / antagonists & inhibitors
  • Purines / chemical synthesis
  • Purines / chemistry
  • Purines / pharmacology*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Protein Kinase Inhibitors
  • Purines
  • Pyrimidines
  • Aurka protein, rat
  • Aurora Kinase A
  • Aurora Kinases
  • Protein Serine-Threonine Kinases
  • Glycogen Synthase Kinase 3