Synthesis And Activities Of The 7-azepanylqunolones

Over the past decades, over twenty quinolones have been launched as antibacterial agents. One of the most notable characteristics of their structures is the presence of the cycloamine group linked at position 7 of the quinolone framework via C-N bond. Here reviewed briefly the history and the structure-activity relationship development of quinolones in this thesis. Eight unreported compounds of two types were successfully synthesized by introducing 4-aminoazepane and 4-hydroxylazepane side-chain to the quinolone frameworks.Starting from benzylamine and ethyl acrylate, the 1-benzylazepane-4-one was successfully synthesized via Dieckmann condensation. It was then converted 4-hydroxylazepane and 4-tertbutoxycarbonyl-aminoazepane, the important side-chain precursors of new compounds. The synthetic process was also optimized in this thesis.All the compounds were tested in vitro against four Gram-positive and four Gram-negative bacteria using the serial two-fold dilution method. Compared with Levofloxacin, all of them not only showed higher or similar activities against Gram-positive organisms, but also moderate to high activities against Gram-negative organisms.The structure-activity relationship showed that 4'-amino and 4'-hydoxyl of 7-azepanyl-quinolones contribute similarly to the antibacterial activity. 7-azepanylquinolones are valuable deserve further study for the future.