Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
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文摘
We report the apparently unprecedented direct reaction of nitric oxide (NO) with amides to generate ions of structure R(C鈺怬)NH鈥揘(O)鈺怤O鈥?/sup>, with examples including R = Me (1a) or 3-pyridyl (1b). The sodium salts of both released NO in pH 7.4 buffer, with 37 掳C half-lives of 1鈥? min. As NO-releasing drug candidates, diazeniumdiolated amides would have the advantage of generating only 1 equiv of base on hydrolyzing exhaustively to NO, in contrast to their amine counterparts, which generate 2 equiv of base.
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