Non-covalent thrombin inhibitors featuring P3-heterocycles with P1-bicyclic arginine surrogates

Bioorg Med Chem Lett. 2002 Oct 21;12(20):2925-30. doi: 10.1016/s0960-894x(02)00585-1.

Abstract

Novel, potent, and highly selective classes of thrombin inhibitors were identified, which resulted from judicious combination of P4-aromatics and P2-P3-heterocyclic dipeptide surrogates with weakly basic (calcd pKa approximately non-basic-8.6) bicyclic P1-arginine mimics. The design, synthesis, and biological activity of achiral, non-covalent, orally bioavailable inhibitors NC1-NC44 featuring P1-indazoles, benzimidazoles, indoles, benzotriazoles, and aminobenzisoxazoles is disclosed.

MeSH terms

  • Animals
  • Area Under Curve
  • Biological Availability
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / pharmacokinetics
  • Bridged Bicyclo Compounds / pharmacology*
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / pharmacokinetics
  • Heterocyclic Compounds, 3-Ring / pharmacology*
  • Indicators and Reagents
  • Rats
  • Structure-Activity Relationship
  • Thrombin / antagonists & inhibitors*
  • Tumor Cells, Cultured

Substances

  • Bridged Bicyclo Compounds
  • Enzyme Inhibitors
  • Heterocyclic Compounds, 3-Ring
  • Indicators and Reagents
  • Thrombin