Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 44, Pages 10813-10824Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01638j
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Funding
- Australian National Health and Medical Research Council (NHMRC)
- Australian Research Council (ARC)
- Avexa Ltd
- Friedrich Naumann Foundation
- German Academic Exchange Service (DAAD)
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Thirty two new binaphthyl-based, functionalized oxazole and thiazole peptidomimetics and over thirty five novel leucine-containing intermediate oxazoles and thiazoles were prepared in this study. This includes the first examples of the direct C-5 arylation of an amino acid dipeptide-derived oxazole. Moderate to excellent antibacterial activity was observed for all new compounds across Gram positive isolates with MICs ranging from 1-16 mu g mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mu g mL(-1) were returned for two examples. Significantly, the in vitro results with a fluoromethyl-oxazole derivative collectively represent the best obtained to date for a member of our binaphthyl peptide antimicrobials.
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