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

Authors

M Robertson
John B. Bremner, University of WollongongFollow
J Coates
John Deadman
Paul A. Keller, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Kittiya SompholFollow
David I. Rhodes, Avexa LtdFollow

RIS ID

38589

Publication Details

Robertson, M., Bremner, J. B., Coates, J., Deadman, J., Keller, P. A., Pyne, S. G., Somphol, K. and Rhodes, D. I. (2011). Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives. European Journal of Medicinal Chemistry, 46 (9), 4201-4211.

Abstract

The synthesis of eleven novel antibacterial agents is reported. The structures are based on a C₂-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. 2011 Elsevier Masson SAS. All rights reserved.