Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

Bioorg Med Chem Lett. 2006 Jul 15;16(14):3706-12. doi: 10.1016/j.bmcl.2006.04.060. Epub 2006 May 6.

Abstract

A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity, and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma.

MeSH terms

  • Animals
  • Asthma / pathology
  • Cells, Cultured
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Hypersensitivity / pathology
  • Jurkat Cells / drug effects
  • Mice
  • Pneumonia / pathology
  • Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Sulfides / chemical synthesis*
  • Sulfides / pharmacology*
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology*

Substances

  • Enzyme Inhibitors
  • Sulfides
  • Thiazoles
  • Protein-Tyrosine Kinases
  • emt protein-tyrosine kinase