Synthesis and antibacterial properties of β-diketone acrylate bioisosteres of pseudomonic acid A

A series of β-diketone acrylate bioisosteres 4 of pseudomonic acid A 1 have been synthesized and evaluated for their ability to inhibit bacterial isoleucyl-tRNA synthetase and act as antibacterial agents. A number of analogues have excellent antibacterial activity. Selected examples were show to aff...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1999-07, Vol.9 (13), p.1847-1852
Main Authors: Bennett, Isobel, Broom, Nigel J.P., Cassels, Robert, Elder, John S., Masson, Nicky D., O'Hanlon, Peter J.
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemical synthesis
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Ketones - blood
Ketones - chemical synthesis
Ketones - pharmacology
Kinetics
Male
Medical sciences
Mice
Mupirocin - analogs & derivatives
Mupirocin - blood
Mupirocin - chemical synthesis
Mupirocin - pharmacology
Pharmacology. Drug treatments
Staphylococcus aureus - metabolism
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Summary:A series of β-diketone acrylate bioisosteres 4 of pseudomonic acid A 1 have been synthesized and evaluated for their ability to inhibit bacterial isoleucyl-tRNA synthetase and act as antibacterial agents. A number of analogues have excellent antibacterial activity. Selected examples were show to afford good blood levels and to be effective in a murine infection model. A series of β-diketone acrylate bioisosteres 4 of pseudomonic acid A have been synthesized and evaluated for their ability to inhibit bacterial isoleucyl-tRNA synthetase and act as antibacterial agents. A number of analogues have excellent antibacterial activity. Selected examples were shown to afford good blood levels and to be effective in a murine infection model.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00296-6