Synthesis and SAR studies of imidazo-[1,2-a]-pyrazine Aurora kinase inhibitors with improved off-target kinase selectivity

Bioorg Med Chem Lett. 2012 May 15;22(10):3544-9. doi: 10.1016/j.bmcl.2012.03.051. Epub 2012 Mar 21.

Abstract

The structure-activity relationships of new Aurora A/B kinase inhibitors derived from the previously identified kinase inhibitor 12 are described. Introduction of acetic acid amides onto the pyrazole of compound 12 was postulated to influence Aurora A/B selectivity and improve the profile against off-target kinases. The SAR of the acetic acid amides was explored and the effect of substitution on enzyme inhibition as well as mechanism-based cell activity was studied. Additionally, several of the more potent inhibitors were screened for their off-target kinase selectivity.

MeSH terms

  • Aurora Kinases
  • Crystallography, X-Ray
  • Imidazoles / pharmacology*
  • Models, Molecular
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Pyrazines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Imidazoles
  • Protein Kinase Inhibitors
  • Pyrazines
  • imidazo(1,2-a)pyrazine
  • Aurora Kinases
  • Protein Serine-Threonine Kinases