Synthetic antibacterials. VI. 7-(1-Substituted 2-(5-nitro-2-furyl)vinyl)-1,8-naphthyridines.

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Abstract
The starting material, ethyl 7-bromomethyl-4-hydroxy-1,8-naphthyridine-3-carboxylate (2), was prepared by the reaction of ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate with Br. Condensation of 2 with 5-nitrofurfural afforded ethyl 7-[1-bromo-2-(5-nitro-2-furyl)vinyl]-4-hydroxy-1,8-naphthyridine-3-carboxylate, which was subsequently hydrolyzed to give 7-[1-bromo-2-(5-nitro-2-furyl)vinyl]-4-hydroxy-1,8-naphthyridine-3-carboxylic acid (4). Alkylation of 4 with alkyl iodide provided 1-alkyl-7-[1-bromo-2-(5-nitro-2-furyl)vinyl]-4-oxo-1,8-naphthyridine-3-carboxylic acid (5 and 6). Nucleophilic displacement of bromine in 4, 5 and 6 afforded the corresponding 7-[1-alkylamino-2-(5-nitro-2-furyl)vinyl]-1,8-naphthyridine derivative. Some members of the series display sufficient antibacterial activity in vitro against both gram-positive and gram-negative bacteria, but none of them was active as the model compound, 1-ethyl-7-[2-(5-nitro-2-furyl)vinyl]-4-oxo-1,8-naphthyridine-3-carboxylic acid.

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