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

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Abstract

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.

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Funding

The reported study was funded by RFBR according to the research project No. 18-43-130004.

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Authors and Affiliations

  1. Department of Organic Chemistry, Physics and Chemistry Institute, National Research Mordovia State University, 68 Bolshevistskaya Str., Saransk, 430005, Russia

    Alexander V. Semenov, Olga I. Balakireva & Irina V. Tarasova

  2. Medicine Institute, National Research Mordovia State University, 68 Bolshevistskaya Str., Saransk, 430005, Russia

    Elena V. Semenova & Polad K. Zulfugarov

Authors
  1. Alexander V. Semenov
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  2. Olga I. Balakireva
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  3. Irina V. Tarasova
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  4. Elena V. Semenova
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  5. Polad K. Zulfugarov
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Correspondence to Alexander V. Semenov.

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Semenov, A.V., Balakireva, O.I., Tarasova, I.V. et al. Synthesis, radical scavenging, and antioxidant activity of stilbazolic resveratrol analogs. Med Chem Res 29, 1590–1599 (2020). https://doi.org/10.1007/s00044-020-02585-6

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  • DOI: https://doi.org/10.1007/s00044-020-02585-6

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