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Open AccessArticle

Synthesis and Structure-Activity Relationship of Daphnetin Derivatives as Potent Antioxidant Agents

1,†, 2,†, 1, 3, 1,* and 3,*
1
School of Life Science and Medicine, Dalian University of Technology, Panjin 124221, China
2
College of Life Science, Dalian Minzu University, Dalian 116600, China
3
Institute of Interdisciplinary Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2018, 23(10), 2476; https://doi.org/10.3390/molecules23102476
Received: 12 September 2018 / Revised: 23 September 2018 / Accepted: 26 September 2018 / Published: 27 September 2018
(This article belongs to the Special Issue Antioxidants Chemistry and Applications)
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Abstract

In this study, daphnetin 1 was chosen as the lead compound, and C-3 or C-4-substituted daphnetins were designed and synthesized to explore the potential relationship between the antioxidant activities and the chemical structures of daphnetin derivatives. The antioxidant activities of the generated compounds were evaluated utilizing the free radical scavenging effect on 2,2′-diphenyl-1-picrylhydrazyl, 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation, and the ferric reducing power assays, and were then compared with those of the standard antioxidant Trolox. The results showed that the catechol group was the key pharmacophore for the antioxidant activity of the daphnetins. The introduction of an electron-withdrawing hydrophilic group at the C-4 position of daphnetin enhanced the antioxidative capacity, but this trend was not observed for C-3 substitution. In addition, introduction of a a hydrophobic phenyl group exerted negative effects on the antioxidant activity in both the C-3 and C-4 substitutions. Among all of the derivatives tested, the most powerful antioxidant was 4-carboxymethyl daphnetin (compound 9), for which the strongest antioxidant activity was observed in all of the assays. In addition, compound 9 also displayed strong pharmaceutical properties in the form of metabolic stability. To summarize, compound 9 holds great potential to be developed as an antioxidant agent with excellent antioxidant activity and proper pharmacokinetic behavior. View Full-Text
Keywords: daphnetin; antioxidant activity; radical scavenging effect; structure-activity relationship daphnetin; antioxidant activity; radical scavenging effect; structure-activity relationship
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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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Xia, Y.; Chen, C.; Liu, Y.; Ge, G.; Dou, T.; Wang, P. Synthesis and Structure-Activity Relationship of Daphnetin Derivatives as Potent Antioxidant Agents. Molecules 2018, 23, 2476.

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