Synthesis and evaluation of chloromethyl sulfoxides as a new class of selective irreversible cysteine protease inhibitors.
The synthesis and biological evaluation of a new class of selective irreversible cysteine protease inhibitors is described. A set of amino acid based chloromethyl sulfoxides was prepared and they were found to inhibit irreversibly the cysteine protease papain. They were selective for cysteine proteases since no inhibition was found for the serine protease chymotrypsin.
Brouwer
Arwin J
AJ
Department of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, PO Box 80082, NL-3508 TB Utrecht, The Netherlands.
Bunschoten
Anton
A
Liskamp
Rob M J
RM
D018360:Crystallography, X-Ray; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis / Q000145:classification / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D010206:Papain / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013454:Sulfoxides / Q000138:chemical synthesis / Q000145:classification / Q000494:pharmacology
D015853:Cysteine Proteinase Inhibitors; D013454:Sulfoxides; D010206:Papain