synthesis and antibacterial properties of new 8-nitrofluoroquinolone derivatives合成和新8-nitrofluoroquinolone衍生品的抗菌性能.pdf

Molecules 2007, 12, 1240-1258 molecules ISSN 1420-3049 © 2007 by MDPI /molecules Full Paper Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives Yusuf M. Al-Hiari *, Inas Saleh Al-Mazari, Ashok K. Shakya †, Rula M. Darwish and Rana Abu-Dahab Faculty of Pharmacy, University of Jordan, Amman 11942 Jordan † Present address: Department of Medicinal and Pharmaceutical Chemistry, Faculty of Pharmacy and Medical Sciences, Amman University, Amman-19328, Jordan * Author of whom correspondence should be addressed; E-mail: al_hiariyusuf@; Fax: (+962) 6 5339649 Received: 13 May 2007; in revised form: 19 June 2007 / Accepted: 20 June 2007 / Published 30 June 2007 Abstract: The objective of this research was the preparation of new 8-nitrofluoro- quinolone 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 fu