Original articleSynthesis and antibacterial activity of new 7-(aminoazabicycloalkanyl)quinolonecarboxylic acidsPréparation d'une série de nouveaux acides 7-(aminoazabicycloalkanyl)-6-fluoroquinoléine carboxyliques substitués en 1 et évaluation de leurs propriétés antibactériennes

Add time:08/18/2019    Source:sciencedirect.com

A series of novel 7-[amino-substituted azabicycloalkanyl]-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-quinolonecarboxylic acid 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.

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