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Molecules 2018, 23(12), 3161; https://doi.org/10.3390/molecules23123161

Synthesis, In Vitro Biological Evaluation, and Oxidative Transformation of New Flavonol Derivatives: The Possible Role of the Phenyl-N,N-Dimethylamino Group

1
Department of Bioanalytical Chemistry, Faculty of Pharmacy, University of Debrecen, Debrecen H-4032, Hungary
2
Department of Biophysics and Cell Biology, Faculty of Medicine, University of Debrecen, Debrecen H-4032, Hungary
3
Department of Organic Chemistry, Faculty of Science and Technology, University of Debrecen, Debrecen H-4032, Hungary
4
Department of Pharmacology, Faculty of Pharmacy, University of Debrecen, Debrecen H-4032, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Luciano Saso
Received: 13 November 2018 / Revised: 29 November 2018 / Accepted: 29 November 2018 / Published: 30 November 2018
(This article belongs to the Special Issue Chemistry and Pharmacology of Modulators of Oxidative Stress 2018)
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Abstract

Six new flavonols (6af) were synthesized with Claisen–Schmidt and Suzuki reactions and they were fully characterized by spectroscopic methods. In order to evaluate their antioxidant activities, their oxygen radical absorption capacity and ferric reducing antioxidant power were measured, along with their free radical scavenging activity against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and 2,2-diphenyl-1-picrylhydrazylradicals. In addition, their cytotoxicity on H9c2 cardiomyoblast cells was also assessed by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Compounds bearing the phenyl-N,N-dimethylamino group (6a, 6c, and 6e) exhibited promising antioxidant potency and did not have any cytotoxic effect. After a consideration of these data, the oxidative transformation of the 6c compound was investigated in vitro with a chemical Fenton reaction and the identification of the formed oxidation products was performed by mass spectrometry. Two potential metabolites were detected. Based on these results, compound 6c can be a model compound for future developments. Overall, this work has proved the involvement of the phenyl-N,N-dimethylamino group in the antioxidant activity of flavonols. View Full-Text
Keywords: antioxidant; flavonoid; flavonol; cytotoxicity; oxidative metabolism antioxidant; flavonoid; flavonol; cytotoxicity; oxidative metabolism
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Szabados-Furjesi, P.; Pajtas, D.; Barta, A.; Csepanyi, E.; Kiss-Szikszai, A.; Tosaki, A.; Bak, I. Synthesis, In Vitro Biological Evaluation, and Oxidative Transformation of New Flavonol Derivatives: The Possible Role of the Phenyl-N,N-Dimethylamino Group. Molecules 2018, 23, 3161.

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