8-Amino-7-(aryl/hetaryl)fluoroquinolones. An emerging set of synthetic antibacterial agents
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Ala’a A. Al-Akhras
,
Mustafa M. El-Abadelah
,
Lubna F. Abu-Niaaj
Abstract
This study reports the synthesis of seven new 8-amino-7-(aryl/hetaryl)fluoroquinolones and their antibacterial activity against 10 bacteria associated with microbial infections and foodborne illnesses. These fluoroquinolones are prepared via the reactions of selected aryl(hetaryl)boronic acids with ethyl-7chloro-6-fluoro-8-nitroquinolone-3-carboxylate, under Suzuki–Miyaura cross-coupling conditions. Nitro group reduction of the latter resulted in the corresponding 8-aminoquinolone-3-esters which upon hydrolysis formed the respective 8-amino-7-(aryl/hetaryl)-quinolone-3-carboxylic acids. The latter compounds were tested against selected Gram-negative bacteria (Escherichia coli, Salmonella typhimurium, Pseudomonas aeruginosa, Acinetobacter baumannii, and Klebsiella pneumonia) and Gram-positive bacteria (Enterococcus feacalis, Listeria monocytogenes, Streptococcus agalactiae, Staphylococcus epidermidis, and Staphylococcus aureus). The tested fluoroquinolones showed a significant antimicrobial activity against most of the tested bacterial strains. The antimicrobial activity of some of the tested compounds were comparable to or higher than a wide range of standard antibiotics including ampicillin, ciprofloxacin, and imipenem. The results highlight the new synthesized 8-amino-7-(aryl/hetaryl)fluroquinolones as promising candidates for new antimicrobial drugs to treat bacterial infections. This study highlights that the newly synthetic 8-amino-7-(aryl/hetaryl)fluroquinolones are promising candidates for new antimicrobial drugs to treat human diseases including foodborne illnesses.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: We thank the Abdul Hameed Shoman Foundation for financial support (Grant number 5/2020).
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Conflict of interest statement: The authors declare to conflicts of interest regarding this article.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2022-0143).
© 2022 Walter de Gruyter GmbH, Berlin/Boston
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Articles in the same Issue
- Frontmatter
- Editorial
- Organic chemistry and medicinal applications
- Research Articles
- Nitroimidazoles Part 10. Synthesis, crystal structure, molecular docking, and anticancer evaluation of 4-nitroimidazole derivatives combined with piperazine moiety
- Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents
- Design, synthesis and antimicrobial assessments of aminoacetylenic-piperazine nitroimidazole hybrid compounds
- Design, synthesis, and molecular docking study of novel cinnoline derivatives as potential inhibitors of tubulin polymerization
- Thiophene ring-opening reactions VI. Attempted cyclization towards [fused]-tricyclic system involving a thiolate anion and suitably located electrophilic carbon
- Thermodynamic control synthesis of spiro[oxindole-3,3′-pyrrolines] via 1,4-dipolar cycloaddition utilizing imidazo[1,5-a]quinoline
- Bioactive secondary metabolites from Trichoderma viride MM21: structure elucidation, molecular docking and biological activity
- 8-Amino-7-(aryl/hetaryl)fluoroquinolones. An emerging set of synthetic antibacterial agents
