Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light-Mediated Antibacterial Activity

ChemMedChem. 2020 May 19;15(10):851-861. doi: 10.1002/cmdc.202000048. Epub 2020 Apr 2.

Abstract

Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco-friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light.

Keywords: S. aureus; antibiotic resistance; antioxidants; imidazoline; microwave chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Benzothiazoles / antagonists & inhibitors
  • Biphenyl Compounds / antagonists & inhibitors
  • Dose-Response Relationship, Drug
  • Escherichia coli / drug effects*
  • Imidazolines / chemical synthesis
  • Imidazolines / chemistry
  • Imidazolines / pharmacology*
  • Light*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Picrates / antagonists & inhibitors
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship
  • Sulfonic Acids / antagonists & inhibitors

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Benzothiazoles
  • Biphenyl Compounds
  • Imidazolines
  • Picrates
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • 1,1-diphenyl-2-picrylhydrazyl