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- Title
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.
- Authors
Amitina, Svetlana A.; Zaytseva, Elena V.; Dmitrieva, Natalya A.; Lomanovich, Alyona V.; Kandalintseva, Natalya V.; Ten, Yury A.; Artamonov, Ilya A.; Markov, Alexander F.; Mazhukin, Dmitrii G.; Elena G., Bagryanskaya; Derek J., McPhee
- Abstract
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 formed N-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.
- Subjects
OXIDATION-reduction reaction; ANTIOXIDANTS; ELECTRON paramagnetic resonance; PHENOL; NITRONES; CERIUM oxides
- Publication
Molecules, 2020, Vol 25, Issue 14, p3118
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25143118