5-Aryl-2-(3,5-dialkyl-4-hydroxyphenyl)-4,4-dimethyl-4 H -imidazole 3-Oxides and Their Redox Species: How Antioxidant Activity of 1-Hydroxy-2,5-dihydro-1 H -imidazoles Correlates with the Stability of Hybrid Phenoxyl-Nitroxides.

Autor: Amitina SA; Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia., Zaytseva EV; Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia., Dmitrieva NA; Department of Chemistry, Institute of Chemistry of Antioxidants, Novosibirsk State Pedagogical University, Vilyuyskaya Str. 28, 6301026 Novosibirsk, Russia., Lomanovich AV; Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia., Kandalintseva NV; Department of Chemistry, Institute of Chemistry of Antioxidants, Novosibirsk State Pedagogical University, Vilyuyskaya Str. 28, 6301026 Novosibirsk, Russia., Ten YA; Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia., Artamonov IA; Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia., Markov AF; Department of Chemistry, Institute of Chemistry of Antioxidants, Novosibirsk State Pedagogical University, Vilyuyskaya Str. 28, 6301026 Novosibirsk, Russia., Mazhukin DG; Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2020 Jul 08; Vol. 25 (14). Date of Electronic Publication: 2020 Jul 08.
DOI: 10.3390/molecules25143118
Abstrakt: Cyclic nitrones of the imidazole series, containing a sterically hindered phenol group, are promising objects for studying antioxidant activity; on the other hand, they can form persistent hybrid phenoxyl-nitroxyl radicals (HPNs) upon oxidation. Here, a series of 5-aryl-4,4-dimethyl-4 H -imidazole 3-oxides was obtained by condensation of aromatic 2-hydroxylaminoketones with 4-formyl-2,6-dialkylphenols followed by oxidation of the initially formed N -hydroxy derivatives. It was shown that the antioxidant activity of both 1-hydroxy-2,5-dihydroimidazoles and 4 H -imidazole 3-oxides increases with a decrease in steric volume of the alkyl substituent in the phenol group, while the stability of the corresponding HPNs generated from 4 H -imidazole 3-oxides reveals the opposite tendency.
Databáze: MEDLINE
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