Synthesis and Antioxidant Activity of Alkyl N-(9H-Thioxanthen-9-yl)(cyclo)alkylhydrazides

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Abstract

A series of new alkyl N-(9H-thioxanthen-9-yl)(cyclo)alkylhydrazides was obtained for the first time by the reaction of (cyclo)alkylhydrazides, 9H-thioxanthen-9-ol and pyridinium perchlorate in a pyridine medium. The antioxidant activity of alkyl N-(9H-thioxanthen-9-yl)(cyclo)alkylhydrazides was studied. The greatest antioxidant effect was revealed in linear and cyclic N-(9H-thioxanthen-9-yl)(cyclo)alkylhydrazides, the values of which are in the range of 0.72–0.88 from ascorbic acid. The presence of a branched radical in N-(9H-thioxanthen-9-yl)alkylhydrazides significantly reduces the antioxidant properties.

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V. Y. Gorokhov

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0003-3829-5038
Russian Federation, Perm, 614013

S. A. Zabolotnykh

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0001-8307-0386
Russian Federation, Perm, 614013

A. V. Kharitonova

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0002-4791-5799
Russian Federation, Perm, 614013

L. G. Chekanova

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0003-1792-6945
Russian Federation, Perm, 614013

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Supplementary files

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2. Fig. 1. General view of the 4d compound molecule according to X-ray diffraction data, represented by thermal ellipsoids with a 30% probability.

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3. 2. Values of antioxidant activity of alkyl-N-(9H-thioxanthene-9-yl)(cyclo)alkylhydrazides 4a–K.

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4. 3. Spectra of the FRAP solution before and after the addition of ascorbic acid (AC) or compound 4j (l = 10 mm, background – water, CA = 2.5·10-3 mol/l, c4j = 10-3 mol/l).

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5. Scheme 1.

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