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

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

doi:10.1039/c5ob01638j

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

Journal article

Peer reviewed

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

Steven M. Wales, Katherine A. Hammer, Kittiya Somphol, Isabell Kemker, David C. Schroeder, Andrew J. Tague, Zinka Brkic, Amy M. King, Dena Lyras, Thomas V. Riley, …

Organic & Biomolecular Chemistry, Vol.13(44), pp.10813-10824

2015

DOI: https://doi.org/10.1039/c5ob01638j

PMID: 26349598

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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 mu g mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mu g 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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Title: Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics
Authors: Steven M. Wales (Author) - University of Wollongong
Katherine A. Hammer (Author) - University of Western Australia
Kittiya Somphol (Author) - University of Wollongong
Isabell Kemker (Author) - University of Wollongong
David C. Schroeder (Author) - University of Wollongong
Andrew J. Tague (Author) - University of Wollongong
Zinka Brkic (Author) - University of Wollongong
Amy M. King (Author) - Monash University
Dena Lyras (Author) - Monash University
Thomas V. Riley (Author) - University of Western Australia
John B. Bremner (Author) - University of Wollongong
Paul A. Keller (Corresponding Author) - University of Wollongong
Stephen G. Pyne (Corresponding Author) - University of Wollongong
Publication details: Organic & Biomolecular Chemistry, Vol.13(44), pp.10813-10824
Publisher: Royal Society of Chemistry
DOI: 10.1039/c5ob01638j
ISSN: 1477-0539
PMID: 26349598
Organisation Unit: Student Services and Engagement; School of Science, Technology and Engineering
Language: English
Record Identifier: 99707363502621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Organic

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