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Article

Redox Conversions of 5-Methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidinide L-Arginine Monohydrate as a Promising Antiviral Drug

by
Alexandra Ivoilova
1,
Ludmila V. Mikhalchenko
2,
Anton Tsmokalyuk
1,
Marina Leonova
2,
Andrey Lalov
2,
Polina Mozharovskaia
1,
Alisa N. Kozitsina
1,
Alla V. Ivanova
1 and
Vladimir L. Rusinov
1,3,*
1
Institute of Chemical Technology, Ural Federal University, 19, Mira St, 620002 Ekaterinburg, Russia
2
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky Prospect, 119991 Moscow, Russia
3
Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 Sofia Kovalevsky St, 620137 Ekaterinburg, Russia
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(16), 5087; https://doi.org/10.3390/molecules26165087
Submission received: 15 July 2021 / Revised: 17 August 2021 / Accepted: 18 August 2021 / Published: 22 August 2021
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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Abstract

This article presents the results of a study of electrochemical transformations in aqueous and aprotic media of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide l-arginine monohydrate (1a, Triazid) obtained by electrochemical methods and ESR spectroscopy. The effect of pH on the current and the reduction potential of 1a in an aqueous Britton–Robinson buffer solution was studied. It was found that 1a is irreversibly reduced in aqueous acidic media on a glassy carbon electrode in one stage with the participation of six electrons and the formation of 5-methyl-6-amino-7-oxo-1,2,4-triazolo[1,5-a]pyrimidin. The electroreduction of 1a in DMF on a background of tetrabutylammonium salts proceeds in two stages, controlled by the kinetics of second-order reactions. In the first stage, the reduction of 1a is accompanied by protonation by the initial compound of the basic intermediate products formed in the electrode reaction (self-protonation mechanism). The second quasi-reversible stage of the electroreduction 1a corresponds to the formation of a dianion radical upon the reduction of the heterocyclic anion 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidin, which is formed upon the potentials of the first peak. The ESR spectrum of the radical dianion was recorded upon electroreduction of Triazid in the presence of Bu4NOH. The effect of the formation of ion pairs on the reversibility of the second peak of the 1a transformation is shown. A change in the rate and regioselectivity of the protonation of the dianion radical in the presence of Na+ and Li+ ions is assumed. The results of studying the electroreduction of 1a by ESR spectroscopy with a TEMPO trap make it possible to assume the simultaneous formation of both a nitroxyl radical and a radical with the spin density localized on the nitrogen at the 4 position of the six-membered ring.
Keywords: nitro-1,2,4-triazolo[1,5a]pyrimidines; Triazid; nitro group transformations; nitroaromatic compounds; nitroheterocyclic compounds; antiviral drugs; cyclic voltammetry; ESR spectroscopy nitro-1,2,4-triazolo[1,5a]pyrimidines; Triazid; nitro group transformations; nitroaromatic compounds; nitroheterocyclic compounds; antiviral drugs; cyclic voltammetry; ESR spectroscopy
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MDPI and ACS Style

Ivoilova, A.; Mikhalchenko, L.V.; Tsmokalyuk, A.; Leonova, M.; Lalov, A.; Mozharovskaia, P.; Kozitsina, A.N.; Ivanova, A.V.; Rusinov, V.L. Redox Conversions of 5-Methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidinide L-Arginine Monohydrate as a Promising Antiviral Drug. Molecules 2021, 26, 5087. https://doi.org/10.3390/molecules26165087

AMA Style

Ivoilova A, Mikhalchenko LV, Tsmokalyuk A, Leonova M, Lalov A, Mozharovskaia P, Kozitsina AN, Ivanova AV, Rusinov VL. Redox Conversions of 5-Methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidinide L-Arginine Monohydrate as a Promising Antiviral Drug. Molecules. 2021; 26(16):5087. https://doi.org/10.3390/molecules26165087

Chicago/Turabian Style

Ivoilova, Alexandra, Ludmila V. Mikhalchenko, Anton Tsmokalyuk, Marina Leonova, Andrey Lalov, Polina Mozharovskaia, Alisa N. Kozitsina, Alla V. Ivanova, and Vladimir L. Rusinov. 2021. "Redox Conversions of 5-Methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidinide L-Arginine Monohydrate as a Promising Antiviral Drug" Molecules 26, no. 16: 5087. https://doi.org/10.3390/molecules26165087

APA Style

Ivoilova, A., Mikhalchenko, L. V., Tsmokalyuk, A., Leonova, M., Lalov, A., Mozharovskaia, P., Kozitsina, A. N., Ivanova, A. V., & Rusinov, V. L. (2021). Redox Conversions of 5-Methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidinide L-Arginine Monohydrate as a Promising Antiviral Drug. Molecules, 26(16), 5087. https://doi.org/10.3390/molecules26165087

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