Development of thioquinazolinones, allosteric Chk1 kinase inhibitors

Bioorg Med Chem Lett. 2009 Feb 15;19(4):1240-4. doi: 10.1016/j.bmcl.2008.12.076. Epub 2008 Dec 24.

Abstract

A high throughput screening campaign was designed to identify allosteric inhibitors of Chk1 kinase by testing compounds at high concentration. Activity was then observed at K(m) for ATP and at near-physiological concentrations of ATP. This strategy led to the discovery of a non-ATP competitive thioquinazolinone series which was optimized for potency and stability. An X-ray crystal structure for the complex of our best inhibitor bound to Chk1 was solved, indicating that it binds to an allosteric site approximately 13A from the ATP binding site. Preliminary data is presented for several of these compounds.

MeSH terms

  • Binding Sites
  • Checkpoint Kinase 1
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Humans
  • Molecular Conformation
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Kinases / chemistry
  • Protein Kinases / drug effects*
  • Protein Kinases / metabolism
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*

Substances

  • Protein Kinase Inhibitors
  • Quinazolines
  • Protein Kinases
  • CHEK1 protein, human
  • Checkpoint Kinase 1