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Molecules 2007, 12(6), 1240-1258;

Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives

Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942 Jordan
Author to whom correspondence should be addressed.
Received: 13 May 2007 / Revised: 19 June 2007 / Accepted: 20 June 2007 / Published: 30 June 2007
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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 α-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 ≈ 2-5 μg/mL. In conclusion, more lipophilic groups seem to enhance activity against gram positive strains. View Full-Text
Keywords: 8-Nitrofluoroquinolone Derivatives; Fluoroquinolone; Antibacterial Properties 8-Nitrofluoroquinolone Derivatives; Fluoroquinolone; Antibacterial Properties

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Al-Hiari, Y.M.; Al-Mazari, I.S.; Shakya, A.K.; Darwish, R.M.; Abu-Dahab, R. Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives. Molecules 2007, 12, 1240-1258.

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