A convenient method for the construction of triazole-bonded chalcone derivatives from acetophenone: Synthesis and free radical scavenging investigation

Atta Ullah, Nur Rohman, Bayu Ardiansah, Antonius Herry Cahyana, Abdulrahman A. Almehizia

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The substituted 1,2,3-triazole core is prevalent in numerous commercially available drugs utilized for a wide range of clinical applications. Simultaneously, chalcone represents a privileged framework discovered in natural products exhibiting intriguing bioactivities. In this study, we synthesized triazole-bonded chalcone compounds (4ax-4by), starting from a simple aromatic ketone, acetophenone, which underwent aldol condensation to give hydroxychalcone intermediate. In the second step, the hydroxyl group of chalcone compound was adducted with propargyl moiety through propargylation reaction. Then, the propargylated products underwent smooth copper-mediated azide-alkyne cyclization to give the triazole-bonded chalcones as the final products. They were characterized by IR, NMR and HRMS, and evaluated their radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH). Among the tested products, compound 4by was denoted as the most potent derivative which can inhibit DPPH radical in 91.62 ± 0.10% at 500 ppm. • Acetophenone as a simple ketone was modified to triazole-bonded chalcones. • Modification was performed through three steps reaction. • Final products exhibited free radical scavenging activity.

Original languageEnglish
Article number102322
JournalMethodsX
Volume11
DOIs
Publication statusPublished - Dec 2023

Keywords

  • 1,2,3-triazole
  • Chalcone
  • Copper-mediated azide-alkyne cyclization
  • Radical scavenging

Fingerprint

Dive into the research topics of 'A convenient method for the construction of triazole-bonded chalcone derivatives from acetophenone: Synthesis and free radical scavenging investigation'. Together they form a unique fingerprint.

Cite this