Discovery of pyrimidine benzimidazoles as Lck inhibitors: part I

Bioorg Med Chem Lett. 2008 Oct 15;18(20):5618-21. doi: 10.1016/j.bmcl.2008.08.104. Epub 2008 Aug 31.

Abstract

A series of 4-amino-6-benzimidazole-pyrimidines was designed to target lymphocyte-specific tyrosine kinase (Lck), a member of the Src kinase family. Highly efficient parallel syntheses were devised to prepare analogues for SAR studies. A number of these 4-amino-6-benzimidazole-pyrimidines exhibited single-digit nanomolar IC(50)s against Lck in biochemical and cellular assays. These 4-amino-6-benzimidazole-pyrimidines represent a new class of tyrosine kinase inhibitors.

MeSH terms

  • Autoimmune Diseases / drug therapy
  • Benzimidazoles / antagonists & inhibitors*
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Humans
  • Inhibitory Concentration 50
  • Lymphocyte Specific Protein Tyrosine Kinase p56(lck) / antagonists & inhibitors*
  • Models, Chemical
  • Molecular Conformation
  • Protein-Tyrosine Kinases / antagonists & inhibitors
  • Pyrimidines / antagonists & inhibitors*
  • Pyrimidines / chemistry
  • Solubility
  • Structure-Activity Relationship
  • src-Family Kinases / metabolism

Substances

  • Benzimidazoles
  • Pyrimidines
  • Protein-Tyrosine Kinases
  • Lymphocyte Specific Protein Tyrosine Kinase p56(lck)
  • src-Family Kinases
  • pyrimidine