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...

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Published in:Pharmaceuticals (Basel, Switzerland) Switzerland), 2022-05, Vol.15 (5), p.588
Main Authors: Ortega, María J, Parra-Torrejón, Belén, Cano-Cano, Fátima, Gómez-Jaramillo, Laura, González-Montelongo, M Carmen, Zubía, Eva
Format: Article
Language:English
Subjects:
3-arylphthalides
Acids
anti-inflammatory
antioxidant
Antioxidants
cytokines
dehydrative coupling reaction
Hydrocarbons
Inflammation
Natural products
phthalides
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Summary: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 ( ) 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 reduced the expression of the pro-inflammatory cytokines and in RAW 264.7 cells. These results, which are the first account of the anti-inflammatory activity of 3-arylphthalides, suggest that compound could be a promising candidate for more advanced anti-inflammatory studies.
ISSN:1424-8247
1424-8247
DOI:10.3390/ph15050588