Inhibitors of glycolic acid oxidase. 4-Substituted-2,4-dioxobutanoic acid derivatives

Fourteen new 4-substituted 2,4-dioxobutanoic acids have been synthesized. These compounds, all of which contain lipophilic 4-substituents, are potent inhibitors in vitro of porcine liver glycolic acid oxidase. The I50 value of the two most potent representatives, 4-(4'-bromo[1,1'-biphenyl]...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1983-08, Vol.26 (8), p.1196-1200
Main Authors: Williams, H. W. R., Eichler, E., Randall, W. C., Rooney, C. S., Cragoe, E. J., Streeter, K. B., Schwam, H., Michelson, S. R., Patchett, A. A., Taub, D.
Format: Article
Language:English
Subjects:
Alcohol Oxidoreductases - antagonists & inhibitors
Biphenyl Compounds
Butyrates - chemical synthesis
Butyrates - pharmacology
glycollate oxidase
liver
Oxepins
pigs
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Summary:Fourteen new 4-substituted 2,4-dioxobutanoic acids have been synthesized. These compounds, all of which contain lipophilic 4-substituents, are potent inhibitors in vitro of porcine liver glycolic acid oxidase. The I50 value of the two most potent representatives, 4-(4'-bromo[1,1'-biphenyl]-4-yl)-2, 4-dioxobutanoic acid (8) and 4-[4'-[[(3,4-dihydro-3-hydroxy-2H-1, 5-benzodioxepin-3-yl)methyl]thio][1,1'-biphenyl]-4-yl]-2, 4-dioxobutanoic acid (13) is 6 X 10(-8)M.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00362a020