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

S.M. Wales, Kate Hammer, K. Somphol, I. Kemker, D.C. Schröder, A.J. Tague, Z. Brkic, A.M. King, D. Lyras, Thomas Riley, J.B. Bremner, P.A. Keller, S.G. Pyne

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    18 Citations (Scopus)

    Abstract

    © The Royal Society of Chemistry. 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.
    Original languageEnglish
    Pages (from-to)10813-10824
    Number of pages12
    JournalOrganic and Biomolecular Chemistry
    Volume13
    Issue number44
    Early online date3 Sep 2015
    DOIs
    Publication statusPublished - 28 Nov 2015

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