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Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides
Phthalides are a group of compounds with relevant biological activities in different areas such as cytotoxicity, anti-stroke activity, neuroprotection, and inflammation, among others. In this study we designed and synthesized a series of 3-arylphthalide derivatives in order to identify their antioxi...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9144619/ https://www.ncbi.nlm.nih.gov/pubmed/35631414 http://dx.doi.org/10.3390/ph15050588 |
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author | Ortega, María J. Parra-Torrejón, Belén Cano-Cano, Fátima Gómez-Jaramillo, Laura González-Montelongo, M. Carmen Zubía, Eva |
author_facet | Ortega, María J. Parra-Torrejón, Belén Cano-Cano, Fátima Gómez-Jaramillo, Laura González-Montelongo, M. Carmen Zubía, Eva |
author_sort | Ortega, María J. |
collection | PubMed |
description | Phthalides are a group of compounds with relevant biological activities in different areas such as cytotoxicity, anti-stroke activity, neuroprotection, and inflammation, among others. In this study we designed and synthesized a series of 3-arylphthalide derivatives in order to identify their antioxidant and anti-inflammatory activities. The synthetic methodology was established in terms of atom and step economy through a dehydrative coupling reaction between 3-hydroxyphthalide and different properly functionalized arene rings. The evaluation of the antioxidant activity was performed by the ABTS assay and for the anti-inflammatory activity the inhibition of LPS-induced nitric oxide (NO) production in microglial cells Bv.2 and macrophage cells RAW 264.7 was measured. The synthesized compound 3-(2,4-dihydroxyphenyl)phthalide (5a) showed better antioxidant activity than the Trolox standard and caused strong inhibition of NO production in LPS-stimulated Bv.2 and RAW 264.7 cells. In addition, compound 5a reduced the expression of the pro-inflammatory cytokines Il1b and Il6 in RAW 264.7 cells. These results, which are the first account of the anti-inflammatory activity of 3-arylphthalides, suggest that compound 5a could be a promising candidate for more advanced anti-inflammatory studies. |
format | Online Article Text |
id | pubmed-9144619 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-91446192022-05-29 Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides Ortega, María J. Parra-Torrejón, Belén Cano-Cano, Fátima Gómez-Jaramillo, Laura González-Montelongo, M. Carmen Zubía, Eva Pharmaceuticals (Basel) Article Phthalides are a group of compounds with relevant biological activities in different areas such as cytotoxicity, anti-stroke activity, neuroprotection, and inflammation, among others. In this study we designed and synthesized a series of 3-arylphthalide derivatives in order to identify their antioxidant and anti-inflammatory activities. The synthetic methodology was established in terms of atom and step economy through a dehydrative coupling reaction between 3-hydroxyphthalide and different properly functionalized arene rings. The evaluation of the antioxidant activity was performed by the ABTS assay and for the anti-inflammatory activity the inhibition of LPS-induced nitric oxide (NO) production in microglial cells Bv.2 and macrophage cells RAW 264.7 was measured. The synthesized compound 3-(2,4-dihydroxyphenyl)phthalide (5a) showed better antioxidant activity than the Trolox standard and caused strong inhibition of NO production in LPS-stimulated Bv.2 and RAW 264.7 cells. In addition, compound 5a reduced the expression of the pro-inflammatory cytokines Il1b and Il6 in RAW 264.7 cells. These results, which are the first account of the anti-inflammatory activity of 3-arylphthalides, suggest that compound 5a could be a promising candidate for more advanced anti-inflammatory studies. MDPI 2022-05-10 /pmc/articles/PMC9144619/ /pubmed/35631414 http://dx.doi.org/10.3390/ph15050588 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Ortega, María J. Parra-Torrejón, Belén Cano-Cano, Fátima Gómez-Jaramillo, Laura González-Montelongo, M. Carmen Zubía, Eva Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides |
title | Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides |
title_full | Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides |
title_fullStr | Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides |
title_full_unstemmed | Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides |
title_short | Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides |
title_sort | synthesis and antioxidant/anti-inflammatory activity of 3-arylphthalides |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9144619/ https://www.ncbi.nlm.nih.gov/pubmed/35631414 http://dx.doi.org/10.3390/ph15050588 |
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