Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid

Dehydroacetic acid is a common pyrone derivative used commercially as an antibacterial and antifungal agent. Based on the synthesis of dehydroacetic acid (1) from N-hydroxysuccinimdyl acetoacetate, a novel series of enamine-based derivatives were synthesised in order to improve the antibacterial act...

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Detalles Bibliográficos
Autores principales: Baldwin, Alex G., Bevan, Jonathan, Brough, David, Ledder, Ruth, Freeman, Sally
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2017
Materias:
Original Research
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5835058/
https://www.ncbi.nlm.nih.gov/pubmed/29527108
http://dx.doi.org/10.1007/s00044-017-2110-8
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author Baldwin, Alex G.
Bevan, Jonathan
Brough, David
Ledder, Ruth
Freeman, Sally
author_facet Baldwin, Alex G.
Bevan, Jonathan
Brough, David
Ledder, Ruth
Freeman, Sally
author_sort Baldwin, Alex G.
collection PubMed
description Dehydroacetic acid is a common pyrone derivative used commercially as an antibacterial and antifungal agent. Based on the synthesis of dehydroacetic acid (1) from N-hydroxysuccinimdyl acetoacetate, a novel series of enamine-based derivatives were synthesised in order to improve the antibacterial activity of dehydroacetic acid. The antibacterial activities of the synthesised analogues were evaluated against Escherichia coli and Staphylococcus aureus. Derivative 4d (N-Ph) was identified as the most potent inhibitor of S. aureus growth. Overall, derivative 4b (N-Me) showed the best broad-spectrum activity with five-fold greater minimum inhibitory concentration and 11-fold greater minimum biocidal concentration against E. coli when compared to dehydroacetic acid, in addition to improved antibacterial activity against S. aureus.
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spelling pubmed-58350582018-03-09 Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid Baldwin, Alex G. Bevan, Jonathan Brough, David Ledder, Ruth Freeman, Sally Med Chem Res Original Research Dehydroacetic acid is a common pyrone derivative used commercially as an antibacterial and antifungal agent. Based on the synthesis of dehydroacetic acid (1) from N-hydroxysuccinimdyl acetoacetate, a novel series of enamine-based derivatives were synthesised in order to improve the antibacterial activity of dehydroacetic acid. The antibacterial activities of the synthesised analogues were evaluated against Escherichia coli and Staphylococcus aureus. Derivative 4d (N-Ph) was identified as the most potent inhibitor of S. aureus growth. Overall, derivative 4b (N-Me) showed the best broad-spectrum activity with five-fold greater minimum inhibitory concentration and 11-fold greater minimum biocidal concentration against E. coli when compared to dehydroacetic acid, in addition to improved antibacterial activity against S. aureus. Springer US 2017-11-13 2018 /pmc/articles/PMC5835058/ /pubmed/29527108 http://dx.doi.org/10.1007/s00044-017-2110-8 Text en © The Author(s) 2017 This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Original Research
Baldwin, Alex G.
Bevan, Jonathan
Brough, David
Ledder, Ruth
Freeman, Sally
Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
title Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
title_full Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
title_fullStr Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
title_full_unstemmed Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
title_short Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
title_sort synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
topic Original Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5835058/
https://www.ncbi.nlm.nih.gov/pubmed/29527108
http://dx.doi.org/10.1007/s00044-017-2110-8
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