Discovery and SAR of novel 4-thiazolyl-2-phenylaminopyrimidines as potent inhibitors of spleen tyrosine kinase (SYK)

Bioorg Med Chem Lett. 2008 Dec 1;18(23):6231-5. doi: 10.1016/j.bmcl.2008.09.106. Epub 2008 Oct 7.

Abstract

A series of SYK inhibitors based on the phenylamino pyrimidine thiazole lead 4 were prepared and evaluated for biological activity. Lead optimization provided compounds with nanomolar K(i)'s against SYK and potent inhibition in mast cell degranulation assays.

MeSH terms

  • Animals
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Drug Design
  • Intracellular Signaling Peptides and Proteins / antagonists & inhibitors*
  • Mast Cells / drug effects
  • Microsomes, Liver / drug effects
  • Molecular Conformation
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Rats
  • Spleen / enzymology*
  • Structure-Activity Relationship
  • Syk Kinase
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Intracellular Signaling Peptides and Proteins
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Thiazoles
  • Protein-Tyrosine Kinases
  • Syk Kinase
  • Syk protein, rat