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


Ay K., Ispartaloglu B., Halay E., Ay E., YAŞA İ. , KARAYILDIRIM T.

MEDICINAL CHEMISTRY RESEARCH, vol.26, no.7, pp.1497-1505, 2017 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 26 Issue: 7
  • Publication Date: 2017
  • Doi Number: 10.1007/s00044-017-1864-3
  • Title of Journal : MEDICINAL CHEMISTRY RESEARCH
  • Page Numbers: pp.1497-1505
  • Keywords: Azidosugar, 1,2,3-Triazole, Sulfanilamide, Antimicrobial, Click reaction, CARBONIC-ANHYDRASE INHIBITORS, ANTIFUNGAL ACTIVITY, BIOLOGICAL-ACTIVITY, 1,2,3-TRIAZOLE, ANALOGS, DERIVATIVES, TRIAZOLES, ALKYNES, DESIGN

Abstract

4-Sulfanilamido substitued-1,2,3-triazoles conjugated with monosaccharides (8-17) 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.