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

Journal Article


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.

Authors


  •   Wales, Steven M. (external author)
  •   Hammer, Katherine A. (external author)
  •   Somphol, Kittiya (external author)
  •   Kemker, Isabell (external author)
  •   Schröder, David C. (external author)
  •   Tague, Andrew (external author)
  •   Brkic, Zinka (external author)
  •   King, Amy M. (external author)
  •   Lyras, Dena (external author)
  •   Riley, Thomas V. (external author)
  •   Bremner, John B.
  •   Keller, Paul A.
  •   Pyne, Stephen G.

Publication Date


  • 2015

Citation


  • Wales, S. M., Hammer, K. A., Somphol, K., Kemker, I., Schröder, 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.

Scopus Eid


  • 2-s2.0-84946606317

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3322

Number Of Pages


  • 11

Start Page


  • 10813

End Page


  • 10824

Volume


  • 13

Issue


  • 44

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.

Authors


  •   Wales, Steven M. (external author)
  •   Hammer, Katherine A. (external author)
  •   Somphol, Kittiya (external author)
  •   Kemker, Isabell (external author)
  •   Schröder, David C. (external author)
  •   Tague, Andrew (external author)
  •   Brkic, Zinka (external author)
  •   King, Amy M. (external author)
  •   Lyras, Dena (external author)
  •   Riley, Thomas V. (external author)
  •   Bremner, John B.
  •   Keller, Paul A.
  •   Pyne, Stephen G.

Publication Date


  • 2015

Citation


  • Wales, S. M., Hammer, K. A., Somphol, K., Kemker, I., Schröder, 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.

Scopus Eid


  • 2-s2.0-84946606317

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3322

Number Of Pages


  • 11

Start Page


  • 10813

End Page


  • 10824

Volume


  • 13

Issue


  • 44