A convenient synthesis of a selective gelatinase inhibitor as an antimetastatic agent.
Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a potent and selective inhibitor for human gelatinases (J. Am. Chem. Soc. 2000, 122, 6799-6800), enzymes implicated in a number of diseases, including cancer. This compound is showing excellent promise in animal trials in a number of disease models. Large quantities of this compound were necessary for these studies. A convenient four-step synthetic route for compound 1 is described herein. The synthesis is amenable to scale-up to tens of grams and gives an overall yield of 57% for this important compound.
Lim
In Taek
IT
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Brown
Stephen
S
Mobashery
Shahriar
S
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D018093:Gelatinases / Q000037:antagonists & inhibitors*; D006801:Humans; D015394:Molecular Structure
D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D018093:Gelatinases