Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada.
Org Lett. 2011 Mar 4;13(5):1178-81. doi: 10.1021/ol200053z. Epub 2011 Feb 9.
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.
O(2)-(乙磺羟肟酸)和 O(2)-(N-甲氧基-2-乙磺酰氨甲酰基)重氮-1-基-1,2-二醇盐（4-7），是一种新型的 O(2)-(保护)重氮二醇盐，通过关键的硫代乙酸酯氧化反应合成。一氧化氮释放研究表明，O(2)-(N-甲氧基-2-乙磺酰氨甲酰基)重氮二醇盐 5 和 7 在非生理碱性缓冲液中，在碱性天然氨基酸 Arg 和 His 等碱基，或在生理 pH 7.4 的 PBS 中的非亲核有机碱 DBU 的存在下，通过β-消除裂解反应释放 NO。
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