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Direct reaction of amides with nitric oxide to form diazeniumdiolates.

ABSTRACT: We report the apparently unprecedented direct reaction of nitric oxide (NO) with amides to generate ions of structure R(C?O)NH-N(O)?NO(-), with examples including R = Me (1a) or 3-pyridyl (1b). The sodium salts of both released NO in pH 7.4 buffer, with 37 °C half-lives of 1-3 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.

SUBMITTER: Holland RJ

PROVIDER: S-EPMC4184460 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Direct reaction of amides with nitric oxide to form diazeniumdiolates.

Holland Ryan J RJ Klose John R JR Deschamps Jeffrey R JR Cao Zhao Z Keefer Larry K LK Saavedra Joseph E JE

The Journal of organic chemistry 20140922 19

We report the apparently unprecedented direct reaction of nitric oxide (NO) with amides to generate ions of structure R(C═O)NH-N(O)═NO(-), with examples including R = Me (1a) or 3-pyridyl (1b). The sodium salts of both released NO in pH 7.4 buffer, with 37 °C half-lives of 1-3 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 ...[more]

PMID: 25210948

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