Synthesis and antibacterial activity of C 2-symmetric binaphthyl scaffolded amino acid derivatives

Mark Robertson, John B. Bremner, Jonathan Coates, John Deadman, Paul A. Keller, Stephen G. Pyne, Kittiya Somphol, David I. Rhodes

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7 Citations (Scopus)

Abstract

The synthesis of eleven novel antibacterial agents is reported. The structures are based on a C 2-symmetric binaphthyl scaffold which holds two identical chains consisting of a short linker, a basic amino acid and a small hydrophobic side chain. Antibacterial activity is revealed for a number of derivatives down to an MIC of 2 μg/mL (2 μM) against Staphylococcus aureus - comparable to vancomycin, and an MIC of 31 μg/mL (31 μM) against some vancomycin-resistant enterococcal strains.

Original languageEnglish
Pages (from-to)4201-4211
Number of pages11
JournalEuropean Journal of Medicinal Chemistry
Volume46
Issue number9
DOIs
Publication statusPublished - Sep 2011
Externally publishedYes

Keywords

  • Antibacterial
  • Binaphthyl scaffolds
  • Peptides
  • Resistant bacteria
  • S. aureus
  • VRE

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