Synthesis, Redox Properties and Antibacterial Activity of Hindered Phenols Linked to Heterocycles

Molecules. 2020 May 20;25(10):2370. doi: 10.3390/molecules25102370.

Abstract

A series of benzotriazole, cyclic amides and pyrimidine derivatives, containing 2,6-di-tert-butyl-phenol fragments, were synthesized. The redox properties of obtained compounds were studied using the cyclic voltammetry on a platinum electrode in acetonitrile. The oxidation potentials of all substances were comparable to those of BHT. The obtained compounds were tested for their antibacterial activity, and N-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)isatin (32 μg/mL) exerted good activity against Staphylococcus aureus.

Keywords: antibacterial activity; antioxidants; heterocycles; hindered phenols.

MeSH terms

  • Amides / chemistry
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Humans
  • Oxidation-Reduction / drug effects
  • Phenols / chemical synthesis
  • Phenols / chemistry*
  • Phenols / isolation & purification
  • Phenols / pharmacology
  • Pyrimidines / chemistry
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / pathogenicity
  • Triazoles / chemistry

Substances

  • Amides
  • Anti-Bacterial Agents
  • Antioxidants
  • Phenols
  • Pyrimidines
  • Triazoles
  • 2,6-di-tert-butylphenol
  • benzotriazole
  • pyrimidine