Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities,Journal of Natural Products

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Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-12-13 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00665
Bruno M. Bizzarri ₁ , Lorenzo Botta ₁ , Eliana Capecchi ₁ , Ignacio Celestino ₂ , Paola Checconi ₃ , Anna T. Palamara _{2,

3} , Lucia Nencioni ₃ , Raffaele Saladino ₁

Affiliation

Different catechol and pyrogallol derivatives have been synthesized by oxidation of coumarins with 2-iodoxybenzoic acid (IBX) in DMSO at 25 °C. A high regioselectivity was observed in accordance with the stability order of the incipient carbocation or radical benzylic-like intermediate. The oxidation was also effective in water under heterogeneous conditions by using IBX supported on polystyrene. The new derivatives showed improved antioxidant effects in the DPPH test and inhibitory activity against the influenza A/PR8/H1N1 virus. These data represent a new entry for highly oxidized coumarins showing an antiviral activity possibly based on the control of the intracellular redox value.

中文翻译：

区域选择性IBX介导的具有抗氧化和抗流感活性的香豆素衍生物的合成

通过在25°C的DMSO中用2-碘氧基苯甲酸（IBX）氧化香豆素来合成不同的邻苯二酚和邻苯三酚衍生物。根据初始碳阳离子或自由基苄基样中间体的稳定性顺序，观察到了较高的区域选择性。通过使用负载在聚苯乙烯上的IBX，在异质条件下的水中氧化也很有效。新衍生物在DPPH测试中显示出改善的抗氧化作用，并具有针对A / PR8 / H1N1流感病毒的抑制活性。这些数据代表了可能基于细胞内氧化还原值控制而显示出抗病毒活性的高氧化香豆素的新条目。

更新日期：2017-12-13

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