Studies on quinoline derivatives and related compounds. 5. Synthesis and antimicrobial activity of novel 1-alkoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

Abstract
A series of novel 1-alkoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids was synthesized and screened as antimicrobial agents. The most active compounds in vitro against gram-negative microorganisms and Staphylococcus aureus were 1,4-dihydro-1-methoxy-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid, 1,2,6,9-tetrahydro-6-methoxy-9-oxofuro[3,2-f]quinoline-8-carboxylic acid and 2,3,6,9-tetrahydro-6-methoxy-3-methyl-2,9-dioxothiazolo[5,4-f]quinoline-8-carboxylic acid. These compounds had antigram-negative activity comparable to that of the corresponding N-ethyl derivatives. Their serum levels and urinary recovery rates in rats were significantly improved relative to the latter compounds.

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