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Amidoximes and Oximes: Synthesis, Structure, and Their Key Role as NO Donors

1
Laboratoire de Chimie Physique Macromoléculaire, Université de Lorraine, CNRS, LCPM, F-54000 Nancy, France
2
Laboratoire Réactions et Génie des Procédés, Université de Lorraine, CNRS, LRGP, F-54000 Nancy, France
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(13), 2470; https://doi.org/10.3390/molecules24132470
Received: 20 June 2019 / Revised: 2 July 2019 / Accepted: 2 July 2019 / Published: 5 July 2019
(This article belongs to the Section Bioorganic Chemistry)
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PDF [4899 KB, uploaded 5 July 2019]
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Abstract

Nitric oxide (NO) is naturally synthesized in the human body and presents many beneficial biological effects; in particular on the cardiovascular system. Recently; many researchers tried to develop external sources to increase the NO level in the body; for example by using amidoximes and oximes which can be oxidized in vivo and release NO. In this review; the classical methods and most recent advances for the synthesis of both amidoximes and oximes are presented first. The isomers of amidoximes and oximes and their stabilities will also be described; (Z)-amidoximes and (Z)-oximes being usually the most energetically favorable isomers. This manuscript details also the biomimetic and biological pathways involved in the oxidation of amidoximes and oximes. The key role played by cytochrome P450 or other dihydronicotinamide-adenine dinucleotide phosphate (NADPH)-dependent reductase pathways is demonstrated. Finally, amidoximes and oximes exhibit important effects on the relaxation of both aortic and tracheal rings alongside with other effects as the decrease of the arterial pressure and of the thrombi formation View Full-Text
Keywords: amidoxime; oxime; synthesis; isomerism; nitric oxide; oxidation amidoxime; oxime; synthesis; isomerism; nitric oxide; oxidation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Sahyoun, T.; Arrault, A.; Schneider, R. Amidoximes and Oximes: Synthesis, Structure, and Their Key Role as NO Donors. Molecules 2019, 24, 2470.

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