Studies on 2-phenylquinoline Staphylococcus aureus NorA efflux pump inhibitors: New insights on the C-6 position

Eur J Med Chem. 2018 Jul 15:155:428-433. doi: 10.1016/j.ejmech.2018.06.013. Epub 2018 Jun 6.

Abstract

The alarming and rapid spread of antimicrobial resistance among bacteria represents a high risk for global health. Targeting factors involved in resistance to restore the activity of failing antibiotics is a promising strategy to overcome this urgent medical need. Efflux pump inhibitors are able to increase antibiotic concentrations in bacteria, thus they can be considered true antimicrobial resistance breakers. In this work, continuing our studies on inhibitors of the Staphylococcus aureus NorA pump, we designed, synthesized and biologically evaluated novel 2-phenylquinoline derivatives starting from our hits 1 and 2. Two of the synthesized compounds (6 and 7) bearing a C-6 benzyloxy group showed the best NorA inhibition activity, thereby providing an excellent starting point to direct future chemical optimizations.

Keywords: Antibiotic resistance breakers; Antimicrobial resistance; Benzyloxy-2-phenylquinoline derivatives; Efflux pump inhibitors; NorA efflux pump; Staphylococcus aureus.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / metabolism
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Hep G2 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Multidrug Resistance-Associated Proteins / antagonists & inhibitors*
  • Multidrug Resistance-Associated Proteins / metabolism
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / metabolism
  • Structure-Activity Relationship

Substances

  • 2-phenylquinoline
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Multidrug Resistance-Associated Proteins
  • Quinolines
  • NorA protein, Staphylococcus