Synthesis and antibacterial activity of new 7-(aminoazabicycloalkanyl)quinolonecarboxylic acids

Article abstract of DOI:10.1016/0223-5234(91)90131-6

A series of novel 7--6-fluoro-1-substituted quinolinecarboxylic acids (18-53) have been prepared and their antibacterial activities evaluated.These compounds are characterized structurally by a new amino-substituted azabicyclo<3.3.0>octane, -<4.3.0>nonane and -<5.3.0>decane ring systems at the 7-position of quinolonecarboxylic acids.To compare the biological activities of enantiomers, (+)-7<(1S,5R)- and (-)-7<(1R,5S)-1-aminomethyl-3-azabicyclo<3.3.0>-octan-3-yl>-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolonecarboxylicacid hydrochloride (43, 44) were synthesized and evaluated for antibacterial activity.Compound 43 was more potent than 44 against both Gram-positive and Gram-negative organisms.The structure-activity relationships of these quinolonecarboxylic acids are also discussed. antibacterial activity / amino-substituted azabicycloalkane ring / substituted quinolonecarboxylic acids / structure-activity relationships