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Oxidation of 4,6-Dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles with Potassium Ferricyanide: Synthesis and Molecular Docking of Bis(pyrid-2-yl) Disulfides

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Abstract

The reaction of 4,6-dimethyl-2-thioxo-1,2-dihydropyridin-3-carbonitriles with K3[Fe(CN)6] in an alkaline medium results in the formation of a mixture of oxidation products: bis(3-cyanopyridin-2-yl) disulfides and potassium 3-cyano-4,6-dimethylpyridine-2-sulfonates. Structure of the compounds was confirmed by NMR, IR spectroscopy and high-resolution mass spectrometry. According to the results of molecular docking studies, 2,2′-dithiobis(5-butyl-4,6-dimethylnicotinonitrile) exhibits affinity to the zinc finger domain of the HIV-1 p7 nucleocapsid protein binding.

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ACKNOWLEDGMENTS

The research was carried out using the equipment of the scientific and educational center “Diagnostics of the structure and properties of nanomaterials” and the equipment of the center for collective Use “Ecological and Analytical Center” of the Kuban State University.

Funding

The work was carried out with the financial support of the Ministry of education and science of the Russian Federation (project FSRN-2023-0005) and the North-Caucasus federal university (interdisciplinary project “Synthesis and antidote activity against the 2,4-D herbicide of heterocyclic derivatives of methylenactive nitriles” within the framework of the strategic academic leadership program “PRIORITY 2030”).

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Authors and Affiliations

  1. Kuban State University, 350040, Krasnodar, Russia

    P. G. Dakhno, V. K. Kindop, V. V. Dotsenko & A. Z. Temerdashev

  2. Kuban State Medical University, 350063, Krasnodar, Russia

    K. V. Gordeev & I. A. Zimmer

  3. North Caucasus Federal University, 355009, Stavropol, Russia

    V. V. Dotsenko, N. A. Aksenov & I. V. Aksenova

  4. Kuban State Technological University, 350072, Krasnodar, Russia

    V. K. Vasilin

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  1. P. G. Dakhno
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Dakhno, P.G., Kindop, V.K., Gordeev, K.V. et al. Oxidation of 4,6-Dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles with Potassium Ferricyanide: Synthesis and Molecular Docking of Bis(pyrid-2-yl) Disulfides. Russ J Gen Chem 93, 3043–3054 (2023). https://doi.org/10.1134/S1070363223120034

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