Design and synthesis of dipeptidyl nitriles as potent, selective, and reversible inhibitors of cathepsin C

Bioorg Med Chem Lett. 2009 Sep 15;19(18):5392-6. doi: 10.1016/j.bmcl.2009.07.114. Epub 2009 Jul 28.

Abstract

A series of dipeptide nitriles with a thienyl alanine in P2 were identified as potent and selective cathepsin C inhibitors. Incorporation of a substituted cyclopropyl moiety in P1 effectively protects these derivatives against hydrolase activity in whole blood.

MeSH terms

  • Animals
  • Cathepsin C / antagonists & inhibitors*
  • Cathepsin C / metabolism*
  • Cell Line
  • Dipeptides / blood
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry*
  • Dipeptides / pharmacology*
  • Humans
  • Nitriles / blood
  • Nitriles / chemical synthesis
  • Nitriles / chemistry*
  • Nitriles / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • Dipeptides
  • Nitriles
  • Cathepsin C