Ammonium-Charged Sterically Hindered Phenols with Antioxidant and Selective Anti-Gram-Positive Bacterial Activity

Chem Biodivers. 2020 May;17(5):e2000147. doi: 10.1002/cbdv.202000147. Epub 2020 Apr 29.

Abstract

The increase in the resistance of pathogens, in particular Staphylococcus aureus, to the action of antibiotics necessitates the search for new readily available and non-toxic drugs. In solving this problem, phenolic acylhydrazones have high potential. In this communication, the synthesis of quaternary ammonium compounds containing a differently substituted phenolic moiety has been performed. An initial study of antimicrobial activity showed that these compounds are highly selective against S. aureus and B. cereus. The highest activity (MIC 2.0 μm) was shown by hydrazones containing a catechol fragment. These compounds are more than 3-fold more active against S. aureus and 3-10-fold more active against B. cereus than norfloxacin. Low hemolytic and high antioxidant activities of all new compounds were also established.

Keywords: antimicrobial activity; antioxidant activity; cell membrane permeability; hemolytic activity; hydrazones.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Bacillus cereus / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Quaternary Ammonium Compounds / chemical synthesis
  • Quaternary Ammonium Compounds / chemistry
  • Quaternary Ammonium Compounds / pharmacology*
  • Staphylococcus aureus / drug effects*

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Phenols
  • Quaternary Ammonium Compounds