CH...O and CH...N hydrogen bonds in ligand design: a novel quinazolin-4-ylthiazol-2-ylamine protein kinase inhibitor

J Med Chem. 2005 Feb 24;48(4):1278-81. doi: 10.1021/jm0492249.

Abstract

Aryl CH hydrogen bonds play an important role in the binding of several analogues of a pyrazol-3-ylquinazolin-4-ylamine inhibitor of glycogen synthase kinase 3 (GSK3). Understanding the importance of these CH...O and CH...N hydrogen bonds allowed the design of a novel quinazolin-4-ylthiazol-2-ylamine inhibitor of GSK3 with a structurally confirmed CH...O hydrogen bond to the protein.

MeSH terms

  • Drug Design
  • Glycogen Synthase Kinase 3 / antagonists & inhibitors*
  • Glycogen Synthase Kinase 3 / chemistry*
  • Hydrogen Bonding
  • Isomerism
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Ligands
  • Quinazolines
  • Thiazoles
  • Glycogen Synthase Kinase 3