Copper-catalyzed azide-alkyne cycloaddition (CuAAC) under mild condition in water: Synthesis, catalytic application and biological activities

Touj N., CHAKCHOUK-MTIBAA A., MANSOUR L., HARRATH A. H., AL-TAMIMI J. H., ÖZDEMİR İ., ...Daha Fazla

JOURNAL OF ORGANOMETALLIC CHEMISTRY, cilt.853, ss.49-63, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 853
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.jorganchem.2017.09.024
  • Dergi Adı: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.49-63
  • Anahtar Kelimeler: Copper N-heterocyclic carbene complex, Alkynes, Azides, Click chemistry, Homogeneous catalysis, Biological activities, N-HETEROCYCLIC CARBENES, CLICK CHEMISTRY, INHIBITORY-ACTIVITY, ACIDIC CORROSION, NHC LIGANDS, IN-SITU, COMPLEXES, ACETYLCHOLINESTERASE, DERIVATIVES, REACTIVITY
  • İnönü Üniversitesi Adresli: Evet

Özet

A series of Cu-N-heterocyclic carbene (Cu-NHC) complexes, 3a-c, were synthesized and characterized by spectroscopic methods such as NMR, HRMS and elemental analysis. The performance of these (Cu-NHC) complexes, 3a-c showed excellent activity in 1,3-dipolar cycloaddition reactions between alkynes and azides to obtain 1,4-disubstituted triazoles 6a-d in 80%-91% isolated yields. All obtained complexes especially compounds 3a and 3c, presented significant inhibitory activity against the tested food-borne pathogens and clinical microorganisms. The compound 3a presents against S. aureus a MIC value of 4.8 mg/ml quite similar to that of ampicillin (4 mg/ml) used as standard. Compounds 3a and 3b, from a concentration of 0.5 mg/ml, present an identical scavenging activity to that of the two used controls butylated hydroxytoluene (BHT) and gallic acid (GA). Concerning acetylcholinesterase inhibition activity (AChEI), compound 6a presents an interesting AChEI activity with 68.3% of inhibition. (C) 2017 Published by Elsevier B.V.