Synthesis and antibacterial activity of C2-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

doi:10.1016/j.ejmech.2011.06.024

Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

Eur J Med Chem. 2011 Sep;46(9):4201-11. doi: 10.1016/j.ejmech.2011.06.024. Epub 2011 Jun 25.

Authors

Mark Robertson¹, John B Bremner, Jonathan Coates, John Deadman, Paul A Keller, Stephen G Pyne, Kittiya Somphol, David I Rhodes

Affiliation

¹ School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.

PMID: 21757269
DOI: 10.1016/j.ejmech.2011.06.024

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology*
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Molecular Structure
Spectrometry, Mass, Electrospray Ionization
Staphylococcus aureus / drug effects

Substances

Amino Acids
Anti-Bacterial Agents