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Antioxidant activity of 4-[alkyl(benzyl)sulfanylmethyl]-5-methyl-2,4-dihydro-3H-pyrazol-3-ones

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Abstract

In order to search for efficient antioxidants of the pyrazolone series, sulfur-containing derivatives of 2,4-dihydro-3H-pyrazol-3-one and 1H-pyrazole (1a–e) were studied in the model system of radical chain oxidation of 1,4-dioxane. The antioxidant activity of these compounds was determined. The rate constant for the reaction of peroxyl radicals with inhibitor 1 (k7) and stoichiometric inhibition coefficient (f) were calculated at 333 K. Sulfur-containing 2,4-dihydro-3H-pyrazol-3-ones exhibit a higher antioxidant activity fk7 = (5.7–9.2)·104 L mol−1 s−1) than 4-(pentylsulfanylmethyl)-3,5-dimethyl-1H-pyrazole fk7 ⩽ 2 · 103 L mol−1 s−1), which is possibly due to the presence of the hydroxyl group in the pyrazolone cycle in the hydroxy form. The stoichiometric coefficients of inhibition for 4-(benzylsulfanylmethyl)-5-methyl-, 5-methyl-4-(pentylsulfanylmethyl)-, and 5-methyl-4-(propylsulfanylmethyl)-2,4-dihydro-3H-pyrazol-3-ones f = 0.95–1.3) indicate the “decay” of one peroxyl radical on one inhibitor molecule. In the case of 5-methyl-4-[(2-propylsulfanyl)methyl]-2,4-dihydro-3H-pyrazol-3-one, the stoichiometric coefficient of inhibition decreases f = 0.59).

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Funding

This work was financially supported in the framework of the plan of research works of the Ufa Institute of Chemistry of the Ufa Federal Research Center of the Russian Academy of Sciences (theme No. 122031400201-0).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 69 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    L. R. Yakupova, A. R. Migranov, L. A. Baeva & R. L. Safiullin

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  1. L. R. Yakupova
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  2. A. R. Migranov
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  3. L. A. Baeva
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  4. R. L. Safiullin
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Correspondence to L. R. Yakupova.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2508–2512, October, 2023.

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Yakupova, L.R., Migranov, A.R., Baeva, L.A. et al. Antioxidant activity of 4-[alkyl(benzyl)sulfanylmethyl]-5-methyl-2,4-dihydro-3H-pyrazol-3-ones. Russ Chem Bull 72, 2508–2512 (2023). https://doi.org/10.1007/s11172-023-4053-1

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