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

Robertson, Mark, Bremner, John B., Coates, Jonathan, Deadman, John, Keller, Paul A., Pyne, Stephen G., Somphol, Kittiya, and Rhodes, David I. (2011) Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives. European Journal of Medicinal Chemistry, 46 (9). pp. 4201-4211.

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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.

Item ID: 36840
Item Type: Article (Research - C1)
ISSN: 1768-3254
Keywords: antibacterial, peptides, binaphthyl scaffolds, VRE, S. aureus, resistant bacteria
Funders: National Health and Medical Research Council (NHMRC)
Projects and Grants: NHMRC (303415 and 404528)
Date Deposited: 10 Dec 2014 07:31
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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