Determination of the chain termination rate constants of the radical chain oxidation of organic compounds on antioxidant
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Determination of the chain termination rate constants of the radical chain oxidation of organic compounds on antioxidant molecules by the QSPR method* Yu. Z. Martynova, V. R. Khairullina, R. N. Nasretdinova, G. G. Garifullina, D. S. Mitsukova, A. Ya. Gerchikov, and A. G. Mustafin Bashkir State University, 32 ul. Z. Validi, 450076 Ufa, Republic of Bashkortostan, Russian Federation. E-mail: [email protected] A quantitative analysis of the structure–antioxidant activity relationship was performed for 128 derivatives of phenols, amines, uracil, benzopyrane, and benzofuran using the GUSAR 2013 program. Nine statistically significant QSAR consensus models characterized by a high accuracy of prediction of the chain termination rate constant of oxidation on the antioxidant molecules were constructed. The results of the structural analysis performed in the GUSAR 2013 program are in good agreement with the literature data. Key words: antioxidant activity, antioxidants, QSPR modeling, GUSAR 2013 program, MNA and QNA descriptors.
At the present time, antioxidants are being intensively studied by chemists, biochemists, and pharmacologists. Increased interest in these substances is due to prospects of their use as stabilizers in food, polymer, and fuel industries in order to prevent or reduce the degradation of food and technical products, as well as the application as active components of drugs, for example, anticancer drugs.1—7 It is known3,4 that antioxidants can deactivate both typical radical intermediates and molecular labile oxidation products formed during the oxidation of organic compounds.4—6 In particular, the reactions of oxidation of organic solvents and synthetic polymers are characterized by the formation of highly reactive peroxide radicals.2 Efficient acceptors of these intermediates are natural and synthetic phenols, polyphenols, aromatic amines, aminophenols, pyrroles, and dipyrrinones.5,7,8 However, the presence of antioxidants in food, pharmaceutical, and technical products does not warrant the pronounced retardation of the oxidation.5,9 This is related to changes in the reactivity of antioxidants depending on their structures and on the possibility of inverting antioxidant properties.5 In addition, the antioxidant activity of the same component can vary depending on the nature of the oxidized substrate.5,8 The determination of the quantitative structure—activity relationships (QSAR) or quantitative structure—property relationships (QSPR) of organic compounds is one of the most important and urgent tasks of the modern * Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9—13, 2019, St. Petersburg, Russia).
chemical science. The QSAR/QSPR modeling makes it possible to quantitatively predict specific properties of compounds promising for synthesis on the basis of their structural features and physicochemical parameters, owing to which this trend becomes more and more demanded one in theoretical chemistry. Increased interest in these studies is caused by the
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