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

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

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2020, Volume: 25, Number: 14, Article number : 3118, Pages count : DOI: 10.3390/molecules25143118

Tags

cyclic hydroxylamines; 4H-imidazole 3-oxides; sterically hindered phenols; antioxidants; hybrid phenoxyl-nitroxides; electron paramagnetic resonance

Authors

Amitina Svetlana A. ¹ , Zaytseva Elena, V ¹ , Dmitrieva Natalya A. ² , Lomanovich Alyona, V ¹ , Kandalintseva Natalya, V ² , Ten Yury A. ¹ , Artamonov Ilya A. ¹ , Markov Alexander F. ² , Mazhukin Dmitrii G. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci SB RAS, Novosibirsk Inst Organ Chem, Siberian Branch, Academician Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Pedag Univ, Inst Chem Antioxidants, Dept Chem, Vilyuyskaya Str 28, Novosibirsk 6301026, Russia

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-4H-imidazole 3-oxides was obtained by condensation of aromatic 2-hydroxylaminoketones with 4-formyl-2,6-dialkylphenols followed by oxidation of the initially formedN-hydroxy derivatives. It was shown that the antioxidant activity of both 1-hydroxy-2,5-dihydroimidazoles and 4H-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 4H-imidazole 3-oxides reveals the opposite tendency.

Amitina S.A. , Zaytseva E.V. , Dmitrieva N.A. , Lomanovich A.V. , Kandalintseva N.V. , Ten Y.A. , Artamonov I.A. , Markov A.F. , Mazhukin D.G.
5-Aryl-2-(3,5-dialkyl-4-hydroxyphenyl)-4,4-dimethyl-4H-imidazole 3-Oxides and Their Redox Species: How Antioxidant Activity of 1-Hydroxy-2,5-dihydro-1H-imidazoles Correlates with the Stability of Hybrid Phenoxyl-Nitroxides

Molecules. 2020. V.25. N14. 3118 . DOI: 10.3390/molecules25143118 WOS Scopus

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Published online:

Jul 8, 2020

Web of science	WOS:000554174800001
Scopus	2-s2.0-85088203910
OpenAlex	W3040869171