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Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid.

ABSTRACT: 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.

SUBMITTER: Baldwin AG

PROVIDER: S-EPMC5835058 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid.

Baldwin Alex G AG Bevan Jonathan J Brough David D Ledder Ruth R Freeman Sally S

Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents 20171113 3

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</ ...[more]

PMID: 29527108

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