Synthesis and antibacterial activities of novel pleuromutilin derivatives

Arch Pharm (Weinheim). 2018 Sep;351(9):e1800155. doi: 10.1002/ardp.201800155. Epub 2018 Jul 29.

Abstract

Pleuromutilin derivatives 4a-h, 5a-g, and 6a-d were synthesized and characterized by IR, 1 H NMR, and 13 C NMR. All synthetic compounds were screened for their in vitro antibacterial activity against Staphylococcus aureus (ATCC 25923), methicillin-resistant S. aureus (MRSA, ATCC 43300), Pasteurella multocida (CVCC 408), Escherichia coli (ATCC 25922), and Salmonella typhimurium (ATCC 14028). Most compounds with quaternary amine showed higher antibacterial activities against both Gram-positive and Gram-negative bacteria strains. Among the screened compounds, compound 5a bearing an N,N,N-trimethyl group at the C-14 side chain of pleuromutilin was found to be the most active agent. Furthermore, preliminary molecular docking was performed to predict the binding interaction of the compounds in the binding pocket.

Keywords: antibacterial activity; molecular docking; pleuromutilin derivatives; synthesis.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Cell Line
  • Cell Survival / drug effects
  • Diterpenes / chemical synthesis
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Dose-Response Relationship, Drug
  • Escherichia coli / drug effects*
  • Escherichia coli / growth & development
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Methicillin-Resistant Staphylococcus aureus / growth & development
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Pasteurella multocida / drug effects*
  • Pasteurella multocida / growth & development
  • Pleuromutilins
  • Polycyclic Compounds
  • Rats
  • Salmonella typhimurium / drug effects*
  • Salmonella typhimurium / growth & development
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Diterpenes
  • Polycyclic Compounds