Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde
In this study, three chalcones derived from vanillin were synthesized and characterized: 4-hydroxy-3-methoxychalcone (Chal 1), 2’,4-dihydroxy-3-methoxy-5’-nitrochalcone (Chal 2), and 4’-nitro-4-hydroxy-3-methoxychalcone (Chal 3), due to their documented biological importance, including antitumor an...
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| Language: | English |
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Universidade Federal de Mato Grosso do Sul
2025-05-01
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| Series: | Orbital: The Electronic Journal of Chemistry |
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| Online Access: | https://trilhasdahistoria.ufms.br/index.php/orbital/article/view/21050 |
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| author | Raphaela Pereira Guaringue Vinícius Monteiro Schaffka Magno Roger Antonichen Thiago de Castro Rozada Barbara Celânia Fiorin |
| author_facet | Raphaela Pereira Guaringue Vinícius Monteiro Schaffka Magno Roger Antonichen Thiago de Castro Rozada Barbara Celânia Fiorin |
| author_sort | Raphaela Pereira Guaringue |
| collection | DOAJ |
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In this study, three chalcones derived from vanillin were synthesized and characterized: 4-hydroxy-3-methoxychalcone (Chal 1), 2’,4-dihydroxy-3-methoxy-5’-nitrochalcone (Chal 2), and 4’-nitro-4-hydroxy-3-methoxychalcone (Chal 3), due to their documented biological importance, including antitumor and antioxidant activities. Acid-mediated aldol condensation was employed for synthesis, followed by characterization via NMR spectroscopy. Additionally, conformational analyses were performed using theoretical calculations with GAUSSIAN 09 software, identifying the s-cis conformation as predominant for all chalcones, with NBO calculations indicating hyperconjugative interactions that confer stability to this conformation relative to the evaluated compounds. These results expand the understanding of the structure-activity relationship of these chalcones, highlighting their potential for future pharmacological applications.
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| format | Article |
| id | doaj-art-4d56a4bc13bb44cc926292b7bda83090 |
| institution | OA Journals |
| issn | 1984-6428 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Universidade Federal de Mato Grosso do Sul |
| record_format | Article |
| series | Orbital: The Electronic Journal of Chemistry |
| spelling | doaj-art-4d56a4bc13bb44cc926292b7bda830902025-08-20T02:26:15ZengUniversidade Federal de Mato Grosso do SulOrbital: The Electronic Journal of Chemistry1984-64282025-05-0117210.17807/orbital.v17i2.21050Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehydeRaphaela Pereira Guaringue0Vinícius Monteiro Schaffka1Magno Roger Antonichen2Thiago de Castro Rozada3Barbara Celânia Fiorin4Universidade Estadual de Ponta GrossaUniversidade Estadual de Ponta GrossaUniversidade Estadual de Ponta GrossaUniversidade Estadual de Maringá (UEM)Universidade Estadual de Ponta Grossa In this study, three chalcones derived from vanillin were synthesized and characterized: 4-hydroxy-3-methoxychalcone (Chal 1), 2’,4-dihydroxy-3-methoxy-5’-nitrochalcone (Chal 2), and 4’-nitro-4-hydroxy-3-methoxychalcone (Chal 3), due to their documented biological importance, including antitumor and antioxidant activities. Acid-mediated aldol condensation was employed for synthesis, followed by characterization via NMR spectroscopy. Additionally, conformational analyses were performed using theoretical calculations with GAUSSIAN 09 software, identifying the s-cis conformation as predominant for all chalcones, with NBO calculations indicating hyperconjugative interactions that confer stability to this conformation relative to the evaluated compounds. These results expand the understanding of the structure-activity relationship of these chalcones, highlighting their potential for future pharmacological applications. https://trilhasdahistoria.ufms.br/index.php/orbital/article/view/21050ChalconeNMRDFTNBOVanillinConformational Analysis |
| spellingShingle | Raphaela Pereira Guaringue Vinícius Monteiro Schaffka Magno Roger Antonichen Thiago de Castro Rozada Barbara Celânia Fiorin Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde Orbital: The Electronic Journal of Chemistry Chalcone NMR DFT NBO Vanillin Conformational Analysis |
| title | Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde |
| title_full | Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde |
| title_fullStr | Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde |
| title_full_unstemmed | Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde |
| title_short | Conformational Study, Synthesis, and Characterization of Chalcones Using 4-Hydroxy-3-methoxybenzaldehyde |
| title_sort | conformational study synthesis and characterization of chalcones using 4 hydroxy 3 methoxybenzaldehyde |
| topic | Chalcone NMR DFT NBO Vanillin Conformational Analysis |
| url | https://trilhasdahistoria.ufms.br/index.php/orbital/article/view/21050 |
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