TY - JOUR
T1 - A convenient method for the construction of triazole-bonded chalcone derivatives from acetophenone
T2 - Synthesis and free radical scavenging investigation
AU - Ullah, Atta
AU - Rohman, Nur
AU - Ardiansah, Bayu
AU - Cahyana, Antonius Herry
AU - Almehizia, Abdulrahman A.
N1 - Funding Information:
This work was fully supported by the Directorate of Research and Development, Universitas Indonesia through Hibah PUTI Q2 Batch 3 (Matching Fund) 2022 with contract No. NKB-1453/UN2.RST/HKP.05.00/2022 . The authors would like to express our sincere gratitude to Assoc. Prof. Mohammad Abrar Alam (Department of Chemistry and Physics, Arkansas State University) for helpful discussion. We also thank Mr. Azhar Darlan (Puslabfor, POLRI) and Ms. Pratiwi Puji Lestari, M.Si. (ILRC Laboratory, Universitas Indonesia) for their kind help in recording HRMS and NMR spectra, respectively.
Funding Information:
This work was fully supported by the Directorate of Research and Development, Universitas Indonesia through Hibah PUTI Q2 Batch 3 (Matching Fund) 2022 with contract No. NKB-1453/UN2.RST/HKP.05.00/2022. The authors would like to express our sincere gratitude to Assoc. Prof. Mohammad Abrar Alam (Department of Chemistry and Physics, Arkansas State University) for helpful discussion. We also thank Mr. Azhar Darlan (Puslabfor, POLRI) and Ms. Pratiwi Puji Lestari, M.Si. (ILRC Laboratory, Universitas Indonesia) for their kind help in recording HRMS and NMR spectra, respectively.
Publisher Copyright:
© 2023 The Author(s)
PY - 2023/12
Y1 - 2023/12
N2 - 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.
AB - 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.
KW - 1,2,3-triazole
KW - Chalcone
KW - Copper-mediated azide-alkyne cyclization
KW - Radical scavenging
UR - http://www.scopus.com/inward/record.url?scp=85166919925&partnerID=8YFLogxK
U2 - 10.1016/j.mex.2023.102322
DO - 10.1016/j.mex.2023.102322
M3 - Article
AN - SCOPUS:85166919925
SN - 2215-0161
VL - 11
JO - MethodsX
JF - MethodsX
M1 - 102322
ER -