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Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential

Chalcones, with two connected aromatic rings through an α,β-unsaturated carbonyl skeleton, display diverse biological roles like antimalarial, antibacterial, anticancer, and antioxidant activities. This research focuses on crafting azachalcone derivatives from 2-acetylpyridine and aromatic aldehydes...

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Detalles Bibliográficos
Autores principales: Rohman, Nur, Ardiansah, Bayu, Cahyana, Antonius Herry, Nurhayati
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10590995/
https://www.ncbi.nlm.nih.gov/pubmed/37876829
http://dx.doi.org/10.1016/j.mex.2023.102427
Descripción
Sumario:Chalcones, with two connected aromatic rings through an α,β-unsaturated carbonyl skeleton, display diverse biological roles like antimalarial, antibacterial, anticancer, and antioxidant activities. This research focuses on crafting azachalcone derivatives from 2-acetylpyridine and aromatic aldehydes using l-proline/Et(3)N as a catalyst. Refinements encompass catalyst dosage, solvents, temperature, and post-reaction treatments. The optimized approach employs l-proline (0.15 equiv.)/ Et(3)N (0.30 equiv.) at room temperature in methanol. Derivatives are successfully synthesized in moderate to favorable yields, akin to sodium hydroxide as the benchmark catalyst. Notably, antioxidant assessment via the DPPH method spotlights compound 2b and 2d (100 ppm concentration), showcasing significant antioxidant potency with inhibition percentages of 92.22 % and 74.41 %, respectively. • l-proline/ Et(3)N is successful to use in aldol condensation reaction. • Azachalcones based 2-acetylpyridine were successfully synthesized using the catalyst. • Azachalcones showed antioxidant activity against DPPH radical.