2-Acetyl-4-aminoresorcinol derivatives: synthesis, antioxidant activity and molecular docking studies

In this study, we synthesized new phenolic compounds that have the potential to serve as antioxidants and slow the effects of free radicals and oxidizing agents, which is beneficial for human health. Three resorcinol derivatives (new amide compounds) were generated by acetylation, nitration, and red...

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Bibliographic Details
Published in:Medicinal chemistry research 2018-04, Vol.27 (4), p.1186-1197
Main Authors: Guerra-Vargas, María A., Rosales-Hernández, Martha C., Martínez-Fonseca, Nadhynee, Padilla-Martínez, Itzia, Fonseca-Sabater, Yadira, Martínez-Ramos, Federico
Format: Article
Language:English
Subjects:
Acetylation
Antioxidants
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Chemical synthesis
Derivatives
Enzymes
Free radicals
Molecular docking
Natural products
Nitration
Original Research
Oxidation
Oxidizing agents
Peroxidase
Pharmacology/Toxicology
Phenolic compounds
Phenols
Redox reactions
Resorcinol
Resveratrol
Sulfonic acid
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Summary:In this study, we synthesized new phenolic compounds that have the potential to serve as antioxidants and slow the effects of free radicals and oxidizing agents, which is beneficial for human health. Three resorcinol derivatives (new amide compounds) were generated by acetylation, nitration, and reduction. The structures of the products were determined by spectroscopic methods. The antioxidant activities of the new compounds were evaluated in vitro by redox reactions with the free radicals of the diammonium salt of 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) ( ABTS + ● ) and 1,1-diphenyl-2-picrylhydrazyl (DPPH ● ). The tested compounds showed antioxidant activities similar to that of resveratrol, a natural product known to affect a wide range of intracellular mediators. These derivatives were also submitted to docking simulations to evaluate their possible interactions with the enzyme myeloperoxidase. This analysis showed potential interactions with pockets “A” and “B” in the enzyme, and the best interaction was detected between succinic-amide (4) and pocket A.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-018-2139-3