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

Ay K., Ispartaloğlu B., HALAY E., Ay E., Yaşa İ., KARAYILDIRIM T.

Medicinal Chemistry Research, vol.26, no.7, pp.1497-1505, 2017 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 26 Issue: 7
  • Publication Date: 2017
  • Doi Number: 10.1007/s00044-017-1864-3
  • Journal Name: Medicinal Chemistry Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1497-1505
  • Keywords: 1,2,3-Triazole, Antimicrobial, Azidosugar, Click reaction, Sulfanilamide
  • Uşak University Affiliated: Yes

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.