Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics

Organic & Biomolecular Chemistry
Steven M WalesStephen G Pyne

Abstract

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 μg mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 μg 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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Citations

Jan 21, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Rodrigo GonzálezNancy B Iannucci
Aug 30, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natalia MolchanovaHenrik Franzyk
Apr 21, 2019·Antibiotics·Rajesh KuppusamyNaresh Kumar
Feb 7, 2020·Current Pharmaceutical Design·Maria FesatidouAthina Geronikaki
Jul 12, 2017·Bioscience, Biotechnology, and Biochemistry·Yusuke AminoMotonaka Kuroda
Mar 20, 2021·ACS Medicinal Chemistry Letters·Andrew J TagueStephen G Pyne

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