The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents.
A series of non-basic building blocks was synthesized and introduced to the C7 position of the quinolone nucleus 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid to afford the corresponding fluoroquinolones in 46-85% yield. The antibacterial activity of these new fluoroquinolones was evaluated using a standard broth microdilution technique. The sulfur-containing quinolone, 7-(2-thia-5-azabicyclo[2.2.1]heptan-5-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid exhibited a superior antibacterial activity against quinolone-susceptible and multidrug-resistant strains in comparison with the clinically used fluoroquinolones ciprofloxacin and vancomycin, especially to the Streptococcus pneumonia and multidrug-resistant S. pneumonia clinical isolates.
Huang
Xiaoguang
X
School of Pharmaceutical Science, Sun Yat-Sen University, Guangzhou 510006, China.
Chen
Dongliang
D
Wu
Ning
N
Zhang
Aiqin
A
Jia
Zhenhua
Z
Li
Xingshu
X
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002939:Ciprofloxacin / Q000138:chemical synthesis / Q000494:pharmacology; D015195:Drug Design; D024901:Drug Resistance, Multiple, Bacterial; D024841:Fluoroquinolones / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism; D013296:Streptococcus pneumoniae / Q000378:metabolism; D013329:Structure-Activity Relationship; D014640:Vancomycin / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D002939:Ciprofloxacin; D014640:Vancomycin