Optimization of 2-phenylaminoimidazo[4,5-h]isoquinolin-9-ones: orally active inhibitors of lck kinase

J Med Chem. 2003 Apr 10;46(8):1337-49. doi: 10.1021/jm020446l.

Abstract

The tyrosine kinase p56lck (lck) is essential for T cell activation; thus, inhibitors of lck have potential utility as autoimmune agents. Our initial disclosure of a new class of lck inhibitors based on the phenylaminoimidazoisoquinolin-9-one showed reasonable cellular activity but did not work in vivo upon oral administration. Our current work highlights the further use of rational drug design and molecular modeling to produce a series of lck inhibitors that demonstrate cellular activity below 100 nM and are as efficacious as cyclosporin A in an in vivo mouse model of anti-CD3-induced IL-2 production.

MeSH terms

  • Administration, Oral
  • Animals
  • Antibodies, Monoclonal / pharmacology
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology
  • CD3 Complex / immunology
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Female
  • Humans
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology
  • Interleukin-2 / antagonists & inhibitors
  • Interleukin-2 / biosynthesis
  • Interleukin-2 / blood
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Isoquinolines / pharmacology
  • Jurkat Cells
  • Lymphocyte Specific Protein Tyrosine Kinase p56(lck) / antagonists & inhibitors*
  • Mice
  • Mice, Inbred BALB C
  • Models, Molecular
  • Molecular Conformation
  • Protein Binding
  • Structure-Activity Relationship

Substances

  • Antibodies, Monoclonal
  • Benzimidazoles
  • CD3 Complex
  • Enzyme Inhibitors
  • Immunosuppressive Agents
  • Interleukin-2
  • Isoquinolines
  • Lymphocyte Specific Protein Tyrosine Kinase p56(lck)