Synthesis and antibacterial properties of new 8-nitrofluoroquinolone derivatives

The objective of this research was the preparation of new 8-nitrofluoroquinolone models and investigation of their antibacterial properties. The work initially involved large scale preparation of the synthon 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3), fo...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2007-06, Vol.12 (6), p.1240-1258
Main Authors: Al-Hiari, Yusuf M, Al-Mazari, Inas Saleh, Shakya, Ashok K, Darwish, Rula M, Abu-Dahab, Rana
Format: Article
Language:English
Subjects:
8-Nitrofluoroquinolone Derivatives
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial Properties
Biological activity
Fluoroquinolone
Fluoroquinolones - chemical synthesis
Fluoroquinolones - chemistry
Fluoroquinolones - pharmacology
Gram-Negative Bacteria - drug effects
Gram-Positive Bacteria - drug effects
Hydrophobic and Hydrophilic Interactions
Investigations
Microbial Sensitivity Tests
Pharmacy
Spectrum Analysis
Structure-Activity Relationship
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Summary:The objective of this research was the preparation of new 8-nitrofluoroquinolone models and investigation of their antibacterial properties. The work initially involved large scale preparation of the synthon 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3), followed by introduction of substituted primary amine appendages at the C-7 position to give derivatives 9a-g, in which the amino group is appended to substituted benzenes or aromatic heterocycles, is part of a primary alpha-amino acid or just a simple primary aliphatic amine. This nucleophilic aromatic substitution step was a very simple procedure since the 8-nitro group of the above synthon facilitated the addition of weak nucleophiles at C-7. All compounds prepared were fully identified and characterized using NMR, IR, EA and MS, and were consistent with expected structures. The prepared targets and the intermediates have shown interesting antibacterial activity against gram positive and/or gram negative strains. In particular, the p-toluidine, p-chloroaniline and aniline derivatives showed good activity against S. aureus with MIC range approximately 2-5 microg/mL. In conclusion, more lipophilic groups seem to enhance activity against gram positive strains.
ISSN:1420-3049
1420-3049
DOI:10.3390/12061240