Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates

[Image: see text] 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....

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Detalles Bibliográficos
Autores principales: Holland, Ryan J., Klose, John R., Deschamps, Jeffrey R., Cao, Zhao, Keefer, Larry K., Saavedra, Joseph E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184460/
https://www.ncbi.nlm.nih.gov/pubmed/25210948
http://dx.doi.org/10.1021/jo501670e
Descripción
Sumario:[Image: see text] 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.

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