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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier
2023
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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 |
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author | Rohman, Nur Ardiansah, Bayu Cahyana, Antonius Herry Nurhayati |
author_facet | Rohman, Nur Ardiansah, Bayu Cahyana, Antonius Herry Nurhayati |
author_sort | Rohman, Nur |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-10590995 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-105909952023-10-24 Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential Rohman, Nur Ardiansah, Bayu Cahyana, Antonius Herry Nurhayati MethodsX Chemistry 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. Elsevier 2023-10-12 /pmc/articles/PMC10590995/ /pubmed/37876829 http://dx.doi.org/10.1016/j.mex.2023.102427 Text en © 2023 The Author(s) https://creativecommons.org/licenses/by/4.0/This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Chemistry Rohman, Nur Ardiansah, Bayu Cahyana, Antonius Herry Nurhayati Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential |
title | Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential |
title_full | Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential |
title_fullStr | Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential |
title_full_unstemmed | Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential |
title_short | Preparation of azachalcone derivatives vial-proline/ Et(3)N-catalyzed aldol condensation and study of their antioxidant potential |
title_sort | preparation of azachalcone derivatives vial-proline/ et(3)n-catalyzed aldol condensation and study of their antioxidant potential |
topic | Chemistry |
url | 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 |
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