Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: heterocyclic P3

Bioorg Med Chem Lett. 2006 Apr 1;16(7):1975-80. doi: 10.1016/j.bmcl.2005.12.095. Epub 2006 Jan 30.

Abstract

A series of N(alpha)-2-benzoxazolyl-alpha-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported.

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology*
  • Animals
  • Cathepsins / antagonists & inhibitors*
  • Cathepsins / chemistry
  • Cathepsins / genetics
  • Cathepsins / physiology
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology*
  • Mice
  • Mice, Knockout
  • Models, Molecular
  • Rats

Substances

  • Amides
  • Enzyme Inhibitors
  • Heterocyclic Compounds
  • Cathepsins
  • cathepsin S