Studies on quinoline derivatives and related compounds. 5. Synthesis and antimicrobial activity of novel 1-alkoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids.
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 (22), 1,2,6,9-tetrahydro-6-methoxy-9-oxofuro[3,2-f]quinoline-8-carboxylic acid (30, and 2,3,6,9-tetrahydro-6-methoxy-3-methyl -2,9-dioxothiazolo [5,4-f]quinoline-8-carboxylic acid (34). These compounds had antigram-negative activity comparable to that of the corresponding N-ethyl derivatives 1, 2, and 4. Their serum levels and urinary recovery rates in rats, however, were significantly improved relative to the latter compounds (1,2, and 4).
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000627:therapeutic use; D004755:Enterobacteriaceae / Q000187:drug effects; D004927:Escherichia coli Infections / Q000188:drug therapy; D007408:Intestinal Absorption; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D008826:Microbial Sensitivity Tests; D011512:Proteus Infections / Q000188:drug therapy; D011513:Proteus mirabilis; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011804:Quinolines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology / Q000627:therapeutic use; D051381:Rats; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D011804:Quinolines