Optimization of HNO Production from N,O-bis-Acylated Hydroxylamine Derivatives

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...

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Veröffentlicht in:	Organic letters 2012-01, Vol.14 (2), p.472-475
Hauptverfasser:	Sutton, Art D, Williamson, Morgan, Weismiller, Hilary, Toscano, John P
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation Cytochrome P-450 Enzyme System - metabolism Esterases - chemistry Hydroxylamine - chemistry Molecular Structure Nitrogen Oxides - chemical synthesis
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description	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.
doi_str_mv	10.1021/ol203016c
format	Article
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subjects	Acylation Cytochrome P-450 Enzyme System - metabolism Esterases - chemistry Hydroxylamine - chemistry Molecular Structure Nitrogen Oxides - chemical synthesis
title	Optimization of HNO Production from N,O-bis-Acylated Hydroxylamine Derivatives
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