Synthetic antibacterials. V. 7-Substituted 1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids.

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Abstract
The reaction of nalidixic acid with thionyl chloride afforded 1-ethyl-1,4-dihydro-4-oxo-7-trichloromethyl-1,8-naphthyridine-3-carboxylic acid (2) in high yield. Several 7-N-substituted carbamoyl- and 7-(5-substituted benzimidazol-2-yl)-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids were prepared by treatment of 2 with appropriate amine and o-phenylenediamine, respectively. Alkaline treatment of 2 provided unexpected 7-hydroxy derivative, while the action of concentrated H2SO4 gave 3,7-dicarboxylic acids. The in vitro antibacterial activity and strutural requirements of these compounds for broad spectrum activity were also discussed.

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