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

María A. Guerra-Vargas, Martha C. Rosales-Hernández, Nadhynee Martínez-Fonseca, Itzia Padilla-Martínez, Yadira Fonseca-Sabater, Federico Martínez-Ramos

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Abstract

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.

Original languageAmerican English
Pages (from-to)1186-1197
Number of pages12
JournalMedicinal Chemistry Research
Volume27
Issue number4
DOIs
StatePublished - 1 Apr 2018

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Keywords

  • 2-acetyl-4-aminoresorcinol
  • Antioxidant activity
  • Docking
  • Myeloperoxidase
  • Resorcinol
  • Synthesis

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