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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
- Source :
- Molecules, Molecules, Vol 26, Iss 5087, p 5087 (2021), Volume 26, Issue 16
- Publication Year :
- 2021
- Publisher :
- MDPI, 2021.
-
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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland. Funding: This work was supported by the Russian Foundation for Basic Research (RFBR, project No. 19-29-08015 mk).
- Subjects :
- Models, Molecular
NITRO GROUP TRANSFORMATIONS
Pharmaceutical Science
Organic chemistry
nitroaromatic compounds
ELECTRICITY
Medicinal chemistry
MOLECULAR MODEL
Analytical Chemistry
chemistry.chemical_compound
QD241-441
Electricity
CHEMISTRY
TRIAZOLES
Drug Discovery
Electrochemistry
TRIAZID
ANTIVIRUS AGENT
MODELS, MOLECULAR
NITROHETEROCYCLIC COMPOUNDS
Aqueous solution
ANTIVIRAL DRUGS
Regioselectivity
ELECTRONS
Chemistry (miscellaneous)
OXIDATION REDUCTION REACTION
ELECTRON SPIN RESONANCE
Molecular Medicine
ELECTRON
Cyclic voltammetry
Oxidation-Reduction
Radical
Protonation
Electrons
ESR SPECTROSCOPY
Redox
Antiviral Agents
NITROAROMATIC COMPOUNDS
Article
ELECTROCHEMISTRY
antiviral drugs
ANTIVIRAL AGENTS
nitro-1,2,4-triazolo[1,5a]pyrimidines
Physical and Theoretical Chemistry
OXIDATION-REDUCTION
TRIAZOLE DERIVATIVE
nitroheterocyclic compounds
Electron Spin Resonance Spectroscopy
Nitroxyl
Buffer solution
ESR spectroscopy
Triazoles
Triazid
cyclic voltammetry
nitro group transformations
ELECTRON SPIN RESONANCE SPECTROSCOPY
chemistry
CYCLIC VOLTAMMETRY
NITRO-1,2,4-TRIAZOLO[1,5A]PYRIMIDINES
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 26
- Issue :
- 16
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....fa4ece3d5e23c37b4efd6edb1f768960