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Synthesis and antimicrobial evaluation of sulfanilamide- and carbohydrate-derived 1,4-disubstitued-1,2,3-triazoles via click chemistry

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Abstract

4-Sulfanilamido substitued-1,2,3-triazoles conjugated with monosaccharides (817) including d-glucose, d-galactose, d-mannose, and d-fructose were synthesized in good yields from azidosugars with propargyl sulfanilamides using copper catalyst 1,3-dipolar cycloaddition reaction (CuAAC). The structures of new compounds were elucidated by liquid chromatography-mass spectrometry, infrared, one-dimensional- and two-dimensional-nuclear magnetic resonance techniques. All of the new compounds were tested in vitro against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Salmonella typhimurium, Klebsiella pneumoniae, Enterococcus faecalis, Pseudomonas aeruginosa, and Candida albicans for their antibacterial and antifungal activities. Experimental results showed antimicrobial activity with minimum inhibitory concentrations values a ranging from 0.078 to 5.0 mg/mL against test microorganisms.

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Acknowledgments

This work was supported by Manisa Celal Bayar University (Project no: BAP-2014-054) and the authors are grateful to Manisa Celal Bayar University for financial support.

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Correspondence to Kadir Ay.

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Ay, K., Ispartaloğlu, B., Halay, E. et al. Synthesis and antimicrobial evaluation of sulfanilamide- and carbohydrate-derived 1,4-disubstitued-1,2,3-triazoles via click chemistry. Med Chem Res 26, 1497–1505 (2017). https://doi.org/10.1007/s00044-017-1864-3

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