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

Steven M Wales, Katherine A Hammer, Kittiya Somphol, Isabell Kemker, David C Schroder, Andrew J Tague, Zinka Brkic, Amy M King, Dena Lyras, Thomas V Riley, John B Bremner, Paul A Keller, Stephen G Pyne

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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 mug mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mug 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.
Original languageEnglish
Pages (from-to)10813 - 10824
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number44
DOIs
Publication statusPublished - 2015

Cite this

Wales, S. M., Hammer, K. A., Somphol, K., Kemker, I., Schroder, D. C., Tague, A. J., Brkic, Z., King, A. M., Lyras, D., Riley, T. V., Bremner, J. B., Keller, P. A., & Pyne, S. G. (2015). Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics. Organic and Biomolecular Chemistry, 13(44), 10813 - 10824. https://doi.org/10.1039/c5ob01638j