title: Synthesis of chiral 2-(4-phenoxyphenylsulfonylmethyl)thiiranes as selective gelatinase inhibitors.
abstract: [reactions: see text] Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers of compound 1 were each synthesized in this study and were shown to be equally active in inhibition of gelatinases.
authors.affiliation: Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Mijoon
authors.initials: M
authors.lastname: Lee
authors.forename: M Margarida
authors.initials: MM
authors.lastname: Bernardo
authors.forename: Samy O
authors.initials: SO
authors.lastname: Meroueh
authors.forename: Stephen
authors.initials: S
authors.lastname: Brown
authors.forename: Rafael
authors.initials: R
authors.lastname: Fridman
authors.forename: Shahriar
authors.initials: S
authors.lastname: Mobashery
mesh_terms: D001665:Binding Sites; D007700:Kinetics; D020778:Matrix Metalloproteinase 2 / Q000737:chemistry / Q000378:metabolism; D020780:Matrix Metalloproteinase 9 / Q000737:chemistry / Q000378:metabolism; D061965:Matrix Metalloproteinase Inhibitors; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D061965:Matrix Metalloproteinase Inhibitors; D011480:Protease Inhibitors; D013440:Sulfides; C013523:ethylene sulfide; D020778:Matrix Metalloproteinase 2; D020780:Matrix Metalloproteinase 9