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

S.M. Wales; K.A. Hammer; K. Somphol; I. Kemker; D.C. Schröder; A.J. Tague; Z. Brkic; A.M. King; D. Lyras; T.V. Riley; J.B. Bremner; P.A. Keller; S.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

S.M. Wales, K.A. Hammer, K. Somphol, I. Kemker, D.C. Schröder, A.J. Tague, Z. Brkic, A.M. King, D. Lyras, T.V. Riley, …

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

2015

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

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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 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.

Details

Title: Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics
Authors/Creators: S.M. Wales (Author/Creator)
K.A. Hammer (Author/Creator)
K. Somphol (Author/Creator)
I. Kemker (Author/Creator)
D.C. Schröder (Author/Creator)
A.J. Tague (Author/Creator)
Z. Brkic (Author/Creator)
A.M. King (Author/Creator)
D. Lyras (Author/Creator)
T.V. Riley (Author/Creator)
J.B. Bremner (Author/Creator)
P.A. Keller (Author/Creator)
S.G. Pyne (Author/Creator)
Publication Details: Organic and Biomolecular Chemistry, Vol.13(44), pp.10813-10824
Publisher: Royal Society of Chemistry
Identifiers: 991005544919107891
Murdoch Affiliation: Murdoch University
Language: English
Resource Type: Journal article

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Collaboration types: Domestic collaboration
Citation topics: 2 Chemistry; 2.1 Synthesis; 2.1.66 Cross-Coupling
Web Of Science research areas: Chemistry, Organic
ESI research areas: Chemistry