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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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
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author Holland, Ryan J.
Klose, John R.
Deschamps, Jeffrey R.
Cao, Zhao
Keefer, Larry K.
Saavedra, Joseph E.
author_facet Holland, Ryan J.
Klose, John R.
Deschamps, Jeffrey R.
Cao, Zhao
Keefer, Larry K.
Saavedra, Joseph E.
author_sort Holland, Ryan J.
collection PubMed
description [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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spelling pubmed-41844602015-09-11 Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates Holland, Ryan J. Klose, John R. Deschamps, Jeffrey R. Cao, Zhao Keefer, Larry K. Saavedra, Joseph E. J Org Chem [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. American Chemical Society 2014-09-11 2014-10-03 /pmc/articles/PMC4184460/ /pubmed/25210948 http://dx.doi.org/10.1021/jo501670e Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Holland, Ryan J.
Klose, John R.
Deschamps, Jeffrey R.
Cao, Zhao
Keefer, Larry K.
Saavedra, Joseph E.
Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
title Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
title_full Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
title_fullStr Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
title_full_unstemmed Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
title_short Direct Reaction of Amides with Nitric Oxide To Form Diazeniumdiolates
title_sort direct reaction of amides with nitric oxide to form diazeniumdiolates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184460/
https://www.ncbi.nlm.nih.gov/pubmed/25210948
http://dx.doi.org/10.1021/jo501670e
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