O 2-(N-Hydroxy(methoxy)-2-ethanesulfonamido) Protected Diazen-1-ium-1,2-diolates: Nitric Oxide Release via a Base-Induced β-Elimination Cleavage

O 2-(Ethanesulfohydroxamic acid) and O 2-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4−7), a novel type of O 2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O 2-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a β-elimination cleavage reaction.