Synthesis and evaluation of ether and halogenated derivatives of mannopeptimycin glycopeptide antibiotics

Bioorg Med Chem Lett. 2003 Aug 18;13(16):2805-8. doi: 10.1016/s0960-894x(03)00542-0.

Abstract

A number of 6-O-ether and 4-O-ether derivatives of mannopeptimycin-alpha with different steric bulk and lipophilicity were synthesized for structure-activity relationship study. Novel iodo and bromo mannopeptimycin-alpha were also prepared. These compounds were synthesized via electrophilic aromatic substitution. Many of the new ether derivatives exhibited potent antibacterial activity against Gram-positive resistant strains including VRE, MRSA, and PRSP.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Drug Resistance, Bacterial / drug effects
  • Ether / chemistry
  • Glycopeptides*
  • Gram-Positive Bacteria / drug effects
  • Halogens / chemistry
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Glycopeptides
  • Halogens
  • mannopeptimycin
  • Ether