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Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid

Baldwin, Alex, Bevan, Jonathan, Brough, David, Ledder, Ruth and Freeman, Sally 2018. Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid. Medicinal Chemistry Research 27 (3) , pp. 884-889. 10.1007/s00044-017-2110-8

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Biosciences
Publisher: Springer
ISSN: 1054-2523
Date of First Compliant Deposit: 19 March 2018
Date of Acceptance: 2 November 2017
Last Modified: 20 Mar 2018 11:19

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