Searching for Novel Inhibitors of the S. aureus NorA Efflux Pump: Synthesis and Biological Evaluation of the 3-Phenyl-1,4-benzothiazine Analogues

ChemMedChem. 2017 Aug 22;12(16):1293-1302. doi: 10.1002/cmdc.201700286. Epub 2017 Jul 17.

Abstract

Bacterial resistance to antimicrobial agents has become an increasingly serious health problem in recent years. Among the strategies by which resistance can be achieved, overexpression of efflux pumps such as NorA of Staphylococcus aureus leads to a sub-lethal concentration of the antibacterial agent at the active site that in turn may predispose the organism to the development of high-level target-based resistance. With an aim to improve both the chemical stability and potency of our previously reported 3-phenyl-1,4-benzothiazine NorA inhibitors, we replaced the benzothiazine core with different nuclei. None of the new synthesized compounds showed any appreciable intrinsic antibacterial activity, and, in particular, 2-(3,4-dimethoxyphenyl)quinoline (6 c) was able to decrease, in a concentration-dependent manner, the ciprofloxacin MIC against the norA-overexpressing strains S. aureus SA-K2378 (norA++) and SA-1199B (norA+/A116E GrlA).

Keywords: NorA efflux pump; Staphylococcus aureus; antimicrobial resistance (AMR); inhibitors; medicinal 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
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / metabolism*
  • Cell Survival / drug effects
  • Ciprofloxacin / pharmacology
  • Drug Design
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests
  • 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*
  • Thiazines / chemical synthesis
  • Thiazines / chemistry*
  • Thiazines / pharmacology

Substances

  • 1,4-benzothiazine
  • 2-(3,4-dimethoxyphenyl)quinoline
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Multidrug Resistance-Associated Proteins
  • Quinolines
  • Thiazines
  • NorA protein, Staphylococcus
  • Ciprofloxacin