Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities
Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities
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DOI：
10.1021/acs.jnatprod.7b00665
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发表时间：
2017-12-01
影响因子：
5.1
通讯作者：
Saladino, Raffaele
中科院分区：
文献类型：
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作者：
Bizzarri, Bruno M.;Botta, Lorenzo;Saladino, Raffaele
通过在25 ℃下在DMSO中用2-碘酰苯甲酸（IBX）氧化香豆素，合成了不同的邻苯二酚和邻苯三酚衍生物。高的区域选择性，观察到根据初始的碳正离子或自由基苄基类中间体的稳定性顺序。氧化也是有效的，在水中在非均相条件下，通过使用IBX支持聚苯乙烯。新衍生物在DPPH测试中显示出改善的抗氧化作用和对流感A/PR 8/H1N1病毒的抑制活性。这些数据代表了一个新的条目高度氧化的香豆素显示抗病毒活性可能基于细胞内氧化还原值的控制。
Different catechol and pyrogallol derivatives have been synthesized by oxidation of coumarins-with 2-iodoxybenzoic acid (IBX) in DMSO at 25 degrees 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.