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, cilt.26, sa.7, ss.1497-1505, 2017 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 26 Sayı: 7
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1007/s00044-017-1864-3
  • Dergi Adı: Medicinal Chemistry Research
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1497-1505
  • Anahtar Kelimeler: 1,2,3-Triazole, Antimicrobial, Azidosugar, Click reaction, Sulfanilamide
  • Uşak Üniversitesi Adresli: Evet

Özet

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.