Synthesis and in vitro antibacterial activity of 7-(4-alkoxyimino-3-amino-3-methylpiperidin-1-yl)fluoroquinolone derivatives

A series of novel 7-(4-alkoxyimino-3-amino-3-methylpiperidin-1-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H NMR, MS and HRMS. These fluoroquinolones were evaluated for in vitro antibacterial activity against representative Gram-positive and Gram-negative strains....

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Bibliographic Details
Published in:European journal of medicinal chemistry 2009-10, Vol.44 (10), p.4063-4069
Main Authors: Chai, Yun, Wan, Zhi-Long, Wang, Bo, Guo, Hui-Yuan, Liu, Ming-Liang
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Anti-Bacterial Agents - toxicity
Antibacterial activity
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacteria - drug effects
Biological and medical sciences
Cell Survival - drug effects
Cercopithecus aethiops
Fluoroquinolone
Fluoroquinolones - chemical synthesis
Fluoroquinolones - chemistry
Fluoroquinolones - pharmacology
Fluoroquinolones - toxicity
Medical sciences
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Structure-Activity Relationship
Synthesis
Vero Cells
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Summary:A series of novel 7-(4-alkoxyimino-3-amino-3-methylpiperidin-1-yl)fluoroquinolone derivatives were designed, synthesized and characterized by 1H NMR, MS and HRMS. These fluoroquinolones were evaluated for in vitro antibacterial activity against representative Gram-positive and Gram-negative strains. All of the title compounds have considerable activity against the twelve strains, and exhibit exceptional potency in inhibiting the growth of Staphylococcus aureus, Staphylococcus epidermidis and Klebsiella pneumoniae (minimum inhibitory concentration (MIC): 0.06–8 μg/mL). The most active compound 17 is 4-fold more potent than levofloxacin against S. aureus and S. epidermidis, 32-fold more potent than levofloxacin against Streptococcus pneumoniae, and 16-fold more potent than IMB against K. pneumoniae. [Display omitted] A series of novel fluoroquinolone derivatives were designed and synthesized. These compounds had high antibacterial activity against representative Gram-positive and Gram-negative strains.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2009.04.041