Thioether acetamides as P3 binding elements for tetrahydropyrido-pyrazole cathepsin S inhibitors

Bioorg Med Chem Lett. 2010 Apr 1;20(7):2379-82. doi: 10.1016/j.bmcl.2010.01.103. Epub 2010 Feb 8.

Abstract

A series of tetrahydropyrido-pyrazole cathepsin S (CatS) inhibitors with thioether acetamide functional groups were prepared with the goal of improving upon the cellular activity of amidoethylthioethers. This Letter describes altered amide connectivity, in conjunction with changes to other binding elements, resulting in improved potency, as well as increased knowledge of the relationship between this chemotype and human CatS activity.

MeSH terms

  • Acetamides / chemistry
  • Acetamides / pharmacology*
  • Cathepsins / antagonists & inhibitors*
  • Cathepsins / chemistry
  • Cathepsins / metabolism*
  • Cell Line
  • Humans
  • Models, Molecular
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship
  • Sulfides / chemistry
  • Sulfides / pharmacology*

Substances

  • Acetamides
  • Protease Inhibitors
  • Pyrazoles
  • Sulfides
  • pyrazole
  • Cathepsins
  • cathepsin S