Synthesis, radical scavenging, and antioxidant activity of stilbazolic resveratrol analogs

To continue the research on the preparation of resveratrol structural analogs containing the 3-pyridinol fragment, a series of derivatives with an ethyl radical sterically shielding the hydroxyl group was synthesized. It was shown that the ethyl group introduction has an ambiguous effect on the radi...

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Bibliographic Details
Published in:Medicinal chemistry research 2020-09, Vol.29 (9), p.1590-1599
Main Authors: Semenov, Alexander V., Balakireva, Olga I., Tarasova, Irina V., Semenova, Elena V., Zulfugarov, Polad K.
Format: Article
Language:English
Subjects:
Analogs
Antioxidants
Biochemistry
Biomedical and Life Sciences
Biomedicine
Bioorganic Chemistry
Derivatives
Hydroxyl groups
Inorganic Chemistry
Intermediates
Lipid peroxidation
Lipids
Medicinal Chemistry
Mitochondria
Original Research
Pharmacology/Toxicology
Resveratrol
Scavenging
Shielding
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Summary:To continue the research on the preparation of resveratrol structural analogs containing the 3-pyridinol fragment, a series of derivatives with an ethyl radical sterically shielding the hydroxyl group was synthesized. It was shown that the ethyl group introduction has an ambiguous effect on the radical scavenging and antioxidant properties of the stilbazoles studied, which is probably related to the structural features of the resulting radical intermediates. The correlation between the radical scavenging and antioxidant properties of the derivatives studied is established. A number of compounds have been identified that exhibit an antioxidant effect on the mitochondrial membranes lipid peroxidation model, better than the natural prototype and 2-ethyl-6-methylpyridin-3-ol with a related structure used in clinical practice.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-020-02585-6