Alkoxyphenylthiazoles with broad-spectrum activity against multidrug-resistant gram-positive bacterial pathogens

Eur J Med Chem. 2018 May 25:152:318-328. doi: 10.1016/j.ejmech.2018.04.049. Epub 2018 Apr 25.

Abstract

With the continued rise of antibiotic resistance and reduced susceptibility to almost all front-line antibiotics, multidrug-resistant Gram-positive bacterial infections represent an incessant threat to healthcare providers. This study presents a new series of phenylthiazole compounds where two active moieties were combined into one scaffold. The antibacterial activity of the hybrid structures extended to include several clinically-relevant multi-drug resistant pathogens including methicillin-resistant and vancomycin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, vancomycin-resistant enterococci, cephalosporin-resistant and methicillin-resistant Streptococcus pneumoniae, and Listeria monocytogenes. In addition, the most potent compounds, 16a and 17a, exhibited a fast bactericidal mode of action in vitro with low susceptibility to induce bacterial resistance. In addition to its potent spectrum of activity against Gram-positive bacterial pathogens, compound 17a was found to be metabolically stable in rats, with a half-life of 4 h.

Keywords: Antibiotic resistance; Methicillin-resistant Staphylococcus aureus (MRSA); Pharmacokinetics; Vancomycin-resistant Enterococci (VRE).

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Caco-2 Cells
  • Dose-Response Relationship, Drug
  • Drug Resistance, Bacterial / drug effects*
  • Drug Resistance, Multiple / drug effects*
  • Humans
  • Listeria monocytogenes / drug effects*
  • Listeria monocytogenes / growth & development
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Rats
  • Rats, Sprague-Dawley
  • Staphylococcus / drug effects*
  • Staphylococcus / growth & development
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Thiazoles