43633-03-0Relevant articles and documents
Stoichiometric Nitroxyl Photorelease Using the (6-Hydroxy-2-naphthalenyl)methyl Phototrigger
Zhou, Yang,Cink, Ruth B.,Seed, Alexander J.,Simpson, M. Cather,Sampson, Paul,Brasch, Nicola E.
supporting information, p. 1054 - 1057 (2019/05/16)
The design and synthesis of a photoactivatable HNO donor incorporating the (6-hydroxynaphthalen-2-yl)methyl (6,2-HNM) photocage coupled to the trifluoromethanesulfonamidoxy analogue of the well-established HNO generator Piloty's acid is described. The photoactive HNO donor stoichiometrically generates HNO (～98%) at neutral pH conditions, and evidence for concerted C-O and N-S bond cleavage was obtained. The methanesulfonamidoxy analogue primarily undergoes undesired N-O bond cleavage.
Development of Photoactivatable Nitroxyl (HNO) Donors Incorporating the (3-Hydroxy-2-naphthalenyl)methyl Phototrigger
Zhou, Yang,Cink, Ruth B.,Fejedelem, Zachary A.,Cather Simpson,Seed, Alexander J.,Sampson, Paul,Brasch, Nicola E.
, p. 1745 - 1755 (2018/04/17)
A new family of photoactivatable HNO donors of general structure RSO2NHO-PT [where PT represents the (3-hydroxy-2-naphthalenyl)methyl (3,2-HMN) phototrigger] has been developed, which rapidly releases HNO. Photogeneration of HNO was demonstrated using the vitamin B12 derivative aquacobalamin as a trapping agent. The amount of sulfonate RSO2– produced was essentially the same as the amount of HNO released upon photolysis, providing a convenient method to indirectly quantify HNO release. Two competing pathways were also observed; a pathway involving O–N bond cleavage leading to release of a sulfonamide, and a pathway resulting in release of the parent Nhydroxysulfonamide RSO2NHOH (for HNO donors with Me- and Ph-containing leaving groups only). Up to approximately 70 % of the HNO-generating pathway was observed with the CF3-containing leaving group, with HNO generation favored for small percentages of aqueous buffer in the acetonitrile/pH 7.00 phosphate buffer solvent mixture. Characterization of the photoproducts obtained from steady-state irradiation by NMR spectroscopy showed that the desired HNO-generating pathway was less favored for HNO donors with Me- and Ph-containing leaving groups compared to the CF3-containing leaving group, suggesting that the excellent CF3-containing leaving group promotes HNO generation.
SULFONYL ESTERS 1: THE REDUCTION OF TRIBROMOPHENYL SULFONATES WITH MERCAPTIDE ANIONS
Durkin, Kathleen Anne,Langler, Richard Francis,Morrison Nancy Ann
, p. 3070 - 3076 (2007/10/02)
2,4,6-tribromophenyl sulfonates have been shown to undergo unusually efficient reduction by mercaptide anions in hexamethylphosphoramide.The reduction products include the sulfinate anion derived from the sulfonate ester and the disulfide derived from the mercaptide anions.
