Synthesis and docking study of 2-phenylaminopyrimidine Abl tyrosine kinase inhibitors

Bioorg Med Chem Lett. 2011 Dec 1;21(23):6964-8. doi: 10.1016/j.bmcl.2011.09.127. Epub 2011 Oct 7.

Abstract

Six analogs of imatinib, an Abl kinase inhibitor clinically used as a first-line therapeutic agent for chronic myeloid leukaemia (CML), have been synthesized and characterized. And their potency as Abl kinase inhibitors have been screened by a robust virtual screening method developed based on the crystal structure (PDB code 2hyy) of Abl-imatinib complex using Surflex-Docking. The docking results are consistent with the inhibitory potency of the compounds characterized by MS method. And the H-bonds between imatinib analogs and Thr315 and Met318 residues in Abl kinase are shown to be crucial for achieving accurate poses and high binding affinities for the ATP-competitive kinase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides
  • Crystallography, X-Ray
  • Enzyme Activation / drug effects
  • Hydrogen Bonding
  • Imatinib Mesylate
  • Mass Spectrometry
  • Models, Molecular
  • Molecular Structure
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology
  • Proto-Oncogene Proteins c-abl / antagonists & inhibitors*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology

Substances

  • Benzamides
  • Piperazines
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Imatinib Mesylate
  • Proto-Oncogene Proteins c-abl