Synthesis and antibacterial activity of novel lincomycin derivatives. I. Enhancement of antibacterial activities by introduction of substituted azetidines

J Antibiot (Tokyo). 2016 Jun;69(6):440-5. doi: 10.1038/ja.2015.134. Epub 2016 Jan 13.

Abstract

The synthesis and antibacterial activity of (7S)-7-sulfur-azetidin-3-yl lincomycin derivatives are described. Modification was achieved by a simple reaction of (7R)-7-O-methanesulfonyllincomycin and the corresponding substituted azetidine-2-thiol. Several compounds first showed moderate antibacterial activity against Streptococcus pneumoniae and Streptococcus pyogenes with erm gene as lincomycin derivatives.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Azetidines / chemical synthesis
  • Azetidines / chemistry
  • Azetidines / pharmacology*
  • Genes, Bacterial
  • Lincomycin / chemical synthesis
  • Lincomycin / chemistry
  • Lincomycin / pharmacology*
  • Streptococcus pneumoniae / drug effects
  • Streptococcus pneumoniae / genetics
  • Streptococcus pyogenes / drug effects
  • Streptococcus pyogenes / genetics
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Azetidines
  • Lincomycin