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

Steven M Wales; Katherine A Hammer; Kittiya Somphol; Isabell Kemker; David C Schroder; 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

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

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

Microbiology

Research output: Contribution to journal › Article › Research › peer-review

31 Citations (Scopus)

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 mug mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mug 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 language	English
Pages (from-to)	10813 - 10824
Number of pages	12
Journal	Organic & Biomolecular Chemistry
Volume	13
Issue number	44
DOIs	https://doi.org/10.1039/c5ob01638j
Publication status	Published - 2015

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Wales, S. M., Hammer, K. A., Somphol, K., Kemker, I., Schroder, 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 & Biomolecular Chemistry, 13(44), 10813 - 10824. https://doi.org/10.1039/c5ob01638j

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

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 mug mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mug 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.",

author = "Wales, {Steven M} and Hammer, {Katherine A} and Kittiya Somphol and Isabell Kemker and Schroder, {David C} and Tague, {Andrew J} and Zinka Brkic and King, {Amy M} and Dena Lyras and Riley, {Thomas V} and Bremner, {John B} and Keller, {Paul A} and Pyne, {Stephen G}",

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Wales, SM, Hammer, KA, Somphol, K, Kemker, I, Schroder, DC, Tague, AJ, Brkic, Z, King, AM, Lyras, D, Riley, TV, Bremner, JB, Keller, PA & Pyne, SG 2015, 'Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics', Organic & Biomolecular Chemistry, vol. 13, no. 44, pp. 10813 - 10824. https://doi.org/10.1039/c5ob01638j

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T1 - Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics

AU - Wales, Steven M

AU - Hammer, Katherine A

AU - Somphol, Kittiya

AU - Kemker, Isabell

AU - Schroder, David C

AU - Tague, Andrew J

AU - Brkic, Zinka

AU - King, Amy M

AU - Lyras, Dena

AU - Riley, Thomas V

AU - Bremner, John B

AU - Keller, Paul A

AU - Pyne, Stephen G

PY - 2015

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N2 - 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 mug mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mug 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.

AB - 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 mug mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mug 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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DO - 10.1039/c5ob01638j

M3 - Article

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JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 44

ER -

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

Abstract

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