title: Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors.
abstract: A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Mechanistic studies revealed a pH dependent intramolecular oxidative deselenization, with ring closure due to an intramolecular nucleophilic attack of a phenoxide ion. All the benzoxazoles herein reported possessed a primary sulfonamide zinc binding group and showed effective inhibitory action on the enzymes, carbonic anhydrases.
authors.affiliation: Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy. fabrizio.carta@unifi.it.
authors.forename: A
authors.initials: A
authors.lastname: Angeli
authors.forename: T S
authors.initials: TS
authors.lastname: Peat
authors.forename: G
authors.initials: G
authors.lastname: Bartolucci
authors.forename: A
authors.initials: A
authors.lastname: Nocentini
authors.forename: C T
authors.initials: CT
authors.lastname: Supuran
authors.forename: F
authors.initials: F
authors.lastname: Carta
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001583:Benzoxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000577:Amides; D001583:Benzoxazoles; D002257:Carbonic Anhydrase Inhibitors; D016566:Organoselenium Compounds; C081959:selenourea; D014508:Urea; D002256:Carbonic Anhydrases