Novel pyrazolo[1,5-a]pyrimidines as c-Src kinase inhibitors that reduce IKr channel blockade

Bioorg Med Chem. 2008 Jan 15;16(2):909-21. doi: 10.1016/j.bmc.2007.10.068. Epub 2007 Oct 24.

Abstract

To improve the in vitro potency of the c-Src inhibitor 1a and to address its hERG liability, a structure-activity study was carried out, focusing on two regions of the lead compound. The blockade of the delayed cardiac current rectifier K(+) (I(Kr)) channel was overcome by replacing the ethylenediamino group with an amino alcohol group at the 7-position. In addition, modifying the substituents at the 5-position and the side chain groups on the amino alcohols at the 7-position enhanced the intracellular c-Src inhibitory activity and increased central nervous system (CNS) penetration. In the present study, 6l exhibited significant in vivo efficacy in a middle cerebral artery (MCA) occlusion model in rats.

MeSH terms

  • Animals
  • Combinatorial Chemistry Techniques
  • Middle Cerebral Artery / drug effects
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Potassium Channel Blockers / pharmacology*
  • Pyrazoles* / chemical synthesis
  • Pyrazoles* / chemistry
  • Pyrazoles* / pharmacology
  • Pyrimidines* / chemical synthesis
  • Pyrimidines* / chemistry
  • Pyrimidines* / pharmacology
  • Rats
  • src-Family Kinases / antagonists & inhibitors*

Substances

  • Potassium Channel Blockers
  • Pyrazoles
  • Pyrimidines
  • src-Family Kinases