Synthesis and antibacterial evaluation of 1,2,3,4-tetrahydro-4-oxo-1,8-naphthyridine-3-carboxylic acid esters, carbonitriles, and carboxamides

A series of 1,2,3,4-tetrahydro-4-oxo-1,8-naphthyridine-3-carboxylic acid esters, carbonitriles, and carboxamides (2a-k) was synthesized and initially evaluated (dose range 50-400 mg/kg) in mice infected with Escherichia coli. Only two derivatives, the ethyl and butyl esters of 1-ethyl-1,2-dihydro-4-...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-10, Vol.18 (10), p.1038-1041
Main Authors: Santilli, Arthur A, Scotese, Anthony C, Yurchenco, John A
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - pharmacology
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Carboxylic Acids - chemical synthesis
Carboxylic Acids - pharmacology
Escherichia coli - drug effects
Esters
Microbial Sensitivity Tests
Naphthyridines - chemical synthesis
Naphthyridines - pharmacology
Nitriles - chemical synthesis
Nitriles - pharmacology
Proteus mirabilis - drug effects
Proteus vulgaris - drug effects
Salmonella typhi - drug effects
Salmonella typhimurium - drug effects
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Summary:A series of 1,2,3,4-tetrahydro-4-oxo-1,8-naphthyridine-3-carboxylic acid esters, carbonitriles, and carboxamides (2a-k) was synthesized and initially evaluated (dose range 50-400 mg/kg) in mice infected with Escherichia coli. Only two derivatives, the ethyl and butyl esters of 1-ethyl-1,2-dihydro-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid, protected the animals against E. coli and several other gram-negative bacterial pathogenic infections. A pro-drug type of mechanism appears to be operable since neither agent showed in vitro activity.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00244a021