Efficient One-Pot Copper(I)-Catalyzed Azide–Alkyne Cycloaddition in Water: Triazole Synthesis, Catalytic Applications, DFT Studies, and Biological Evaluation

Zouaghi M. O., bouabidi T., Touj N., ÖZDEMİR İ., GÜRBÜZ N., Youssef A., ...Daha Fazla

Chemistry and Biodiversity, cilt.23, sa.5, 2026 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 5
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1002/cbdv.71280
  • Dergi Adı: Chemistry and Biodiversity
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, EMBASE, MEDLINE
  • Anahtar Kelimeler: alkynes, azides, biological activities, click chemistry, copper N-heterocyclic carbene complex, DFT study, homogeneous catalysis
  • İnönü Üniversitesi Adresli: Evet

Özet

A series of Cu–N-heterocyclic carbene (Cu–NHC) complexes (3a–e) was successfully synthesized and their structures verified by NMR, HRMS, and elemental analysis. These complexes displayed excellent catalytic performance in the 1,3-dipolar cycloaddition of alkynes with azides, producing 1,4-disubstituted triazoles (4a–e) in isolated yields of 80%–91%. The cycloaddition between phenylacetylene and various azides was also explored theoretically using DFT/B3LYP/6-311+G(d) methods. The cytotoxic properties of the obtained compounds were evaluated against A549, HCT116, and BEAS-2B cell lines, with several derivatives exhibiting significant anticancer activity. Moreover, their antioxidant potential was assessed through DPPH and ABTS radical-scavenging assays, in which compound 2 showed particularly strong performance.