title: Synthetic Studies on the Preparation of Alanyl Epoxysulfones as Cathepsin Cysteine Protease Electrophilic Traps.
abstract: A Darzens reaction between tert-butoxycarbonyl alaninal and chloromethyl phenyl sulfone afforded chlorohydrins, which were converted into epoxysulfones by reaction with sodium tert-butoxide. Epoxysulfone 10 and chloroketone 14 derived from chlorohydrins by oxidation proved to be inhibitors of cathepsins H, S, and C as determined by competitive activity-based protein profiling.
authors.affiliation: †Departament de Química Inorgànica i Orgànica, Universitat Jaume I, 12080 Castelló, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Latorre
authors.affiliation: †Departament de Química Inorgànica i Orgànica, Universitat Jaume I, 12080 Castelló, Spain.
authors.forename: Santiago
authors.initials: S
authors.lastname: Rodríguez
authors.affiliation: †Departament de Química Inorgànica i Orgànica, Universitat Jaume I, 12080 Castelló, Spain.
authors.forename: Florenci V
authors.initials: FV
authors.lastname: González
authors.affiliation: §Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Bogdan I
authors.initials: BI
authors.lastname: Florea
authors.affiliation: §Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D002728:Chlorohydrins / Q000737:chemistry*; D057056:Cysteine Proteases / Q000138:chemical synthesis* / Q000737:chemistry; D015853:Cysteine Proteinase Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D002728:Chlorohydrins; D015853:Cysteine Proteinase Inhibitors; D004852:Epoxy Compounds; C046025:alaninal; D057056:Cysteine Proteases; D000409:Alanine