Peptidyl allyl sulfones: a new class of inhibitors for clan CA cysteine proteases

Bioorg Med Chem. 2004 Oct 1;12(19):5203-11. doi: 10.1016/j.bmc.2004.07.016.


A new series of peptidyl allyl sulfone inhibitors was discovered while trying to synthesize epoxy sulfone inhibitors from vinyl sulfones using basic oxidizing conditions. The various dipeptidyl allyl sulfones were evaluated with calpain I, papain, cathepsins B and L, cruzain and rhodesain and found to be potent inhibitors. In comparison to the previously developed class of vinyl sulfone inhibitors, the novel dipeptidyl allyl sulfones were more potent inhibitors than the corresponding dipeptidyl vinyl sulfones. It was observed that the stereochemistry of the vinyl sulfone precursor played a role in the potency of the dipeptidyl allyl sulfone inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Cattle
  • Cysteine Endopeptidases / chemistry
  • Cysteine Endopeptidases / drug effects*
  • Cysteine Proteinase Inhibitors / chemical synthesis*
  • Cysteine Proteinase Inhibitors / pharmacology
  • Dipeptides / chemical synthesis
  • Dipeptides / pharmacology
  • Erythrocytes / enzymology
  • Inhibitory Concentration 50
  • Kinetics
  • Structure-Activity Relationship
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry
  • Sulfones / pharmacology


  • Cysteine Proteinase Inhibitors
  • Dipeptides
  • Sulfones
  • divinyl sulfone
  • Cysteine Endopeptidases