The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents.

Abstract

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.

• Authors: Xiaoguang Huang, Dongliang Chen, Ning Wu, Aiqin Zhang, Zhenhua Jia, Xingshu Li
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 19 Issue 15 Pg. 4130-3 (Aug 01 2009) ISSN: 1464-3405 [Electronic] England
• PMID: 19539467 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anti-Bacterial Agents
• Fluoroquinolones
• Ciprofloxacin
• Vancomycin

Topics

• Anti-Bacterial Agents (chemical synthesis, pharmacology)
• Chemistry, Pharmaceutical (methods)
• Ciprofloxacin (chemical synthesis, pharmacology)
• Drug Design
• Drug Resistance, Multiple, Bacterial
• Fluoroquinolones (chemical synthesis, pharmacology)
• Microbial Sensitivity Tests
• Models, Chemical
• Molecular Structure
• Stereoisomerism
• Streptococcus pneumoniae (metabolism)
• Structure-Activity Relationship
• Vancomycin (chemical synthesis, pharmacology)