title: Optimization of HNO production from N,O-bis-acylated hydroxylamine derivatives.
abstract: A wide range of N,O-bis-acylated hydroxylamine derivatives with chloro or arenesulfonyl leaving groups, and a related set of N-hydroxy-N-acylsulfonamides, have been synthesized and evaluated for nitroxyl (HNO) production. Mechanistic studies have revealed that the observed aqueous chemistry is more complicated than originally anticipated, and have been used to develop a new series of efficient HNO precursors (4u-4x, 7c-7d) with tunable half-lives.
authors.affiliation: Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218, USA.
authors.forename: Art D
authors.initials: AD
authors.lastname: Sutton
authors.forename: Morgan
authors.initials: M
authors.lastname: Williamson
authors.forename: Hilary
authors.initials: H
authors.lastname: Weismiller
authors.forename: John P
authors.initials: JP
authors.lastname: Toscano
mesh_terms: D000215:Acylation; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D004950:Esterases / Q000737:chemistry; D019811:Hydroxylamine / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis*
chemical_list: D009589:Nitrogen Oxides; D019811:Hydroxylamine; D003577:Cytochrome P-450 Enzyme System; D004950:Esterases; C039900:nitroxyl