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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| Main Authors: | , , , , , |
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| Format: | Book |
| Published: |
MDPI AG,
2022-05-01T00:00:00Z.
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| Online Access: | Connect to this object online. |
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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 (<b>5a</b>) 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 <b>5a</b> reduced the expression of the pro-inflammatory cytokines <i>Il1b</i> and <i>Il6</i> in RAW 264.7 cells. These results, which are the first account of the anti-inflammatory activity of 3-arylphthalides, suggest that compound <b>5a</b> could be a promising candidate for more advanced anti-inflammatory studies. |
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| Item Description: | 10.3390/ph15050588 1424-8247 |