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Design, synthesis and biological evaluation of 8-aminoquinoline-1,2,3-triazole hybrid derivatives as potential antimicrobial agents

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Abstract

A library of 20 novel quinoline-1,2,3-triazole hybrid compounds were synthesized by starting from 8-aminoquinoline to discover new pharmacophores exhibiting antimicrobial activities. Effective and targeted selective biologically active molecules through conjugation of diversely substituted triazoles and 8-aminoquinoline were achieved successfully with 1,4-disubstituted regioisomer product in the 3 + 2 cycloaddition reaction, as expected. All the synthesized compounds were evaluated for antimicrobial activity against different antibacterial and antifungal pathogenic strains. Pleasingly, the compound 9a was found as the most potent against Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Bacillus subtilis, Candida albicans and Candida parapsilosis strains. Preliminary screening results indicated that triazole linked quinoline compounds demonstrate promising antimicrobial activities against Gram (+) and Gram (−) bacterial and fungi strains. Furthermore, the pharmacokinetic properties of the quinoline-1,2,3-triazole hybrid compounds were analyzed to evaluate their potential as drug candidates, which indicated that all compounds are in agreement with Lipinski’s rule of five.

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Acknowledgements

We would like to thank Prof. Dr. Ramazan Altundaş, Prof. Dr. Öztekin Algül and Prof. Dr. Aylin Döğen for valuable discussions and helpful editorial comment.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Gebze Technical University, 41400, Kocaeli, Turkey

    Fatma Albayrak, Mustafa Çiçek & Irem Kulu

  2. Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, 33169, Mersin, Turkey

    Deniz Alkaya

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  1. Fatma Albayrak
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  2. Mustafa Çiçek
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Correspondence to Irem Kulu.

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Albayrak, F., Çiçek, M., Alkaya, D. et al. Design, synthesis and biological evaluation of 8-aminoquinoline-1,2,3-triazole hybrid derivatives as potential antimicrobial agents. Med Chem Res 31, 652–665 (2022). https://doi.org/10.1007/s00044-022-02866-2

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