Synthesis and Antibacterial Properties of New 8-Nitrofluoro quinolone Derivatives

Molecules

Yusuf M. Al-Hiari¹  Inas Saleh Al-Mazari²  Ashok K. Shakya¹  Rula M. Darwish² 

[1] id="af1-molecules-12-01240">Faculty of Pharmacy, University of Jordan, Amman 11942 Jord

关键词: 8-Nitrofluoroquinolone Derivatives;    Fluoroquinolone;    Antibacterial Properties;   

DOI  :  10.3390/12061240

来源: mdpi

【 摘 要 】

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 9a-g 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-chloro aniline 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.

【 授权许可】

Unknown   
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