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

Authors

Steven M. Wales, University of WollongongFollow
Katherine A. Hammer, University of Western Australia
Kittiya Somphol, University of WollongongFollow
Isabell Kemker, University of WollongongFollow
David C. Schröder, University of Wollongong
Andrew Tague, University of WollongongFollow
Zinka Brkic, University of WollongongFollow
Amy M. King, Monash University
Dena Lyras, Monash University
Thomas V. Riley, University of Western AustraliaFollow
John B. Bremner, University of WollongongFollow
Paul A. Keller, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

103998

Publication Details

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.

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.

Grant Number

NHMRC/1051105

Additional Grant Number

http://purl.org/au-research/grants/NHMRC/1051105