Department of Ecology and Biology, University of Tuscia , Via C. De Lellis, Viterbo, 01100, Italy.
IRCCS, San Raffaele Pisana, Telematic University , Rome, 00163, Italy.
J Nat Prod. 2017 Dec 22;80(12):3247-3254. doi: 10.1021/acs.jnatprod.7b00665. Epub 2017 Dec 13.
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.
不同的儿茶酚和焦酚衍生物已通过在 DMSO 中用 2-碘酰基苯甲酸（IBX）氧化香豆素合成，温度为 25°C。根据初始碳正离子或自由基苄基样中间体的稳定性顺序，观察到高区域选择性。通过在聚苯乙烯上负载 IBX，在非均相条件下的水中，氧化也很有效。新衍生物在 DPPH 测试中显示出更好的抗氧化效果，对甲型流感病毒/PR8/H1N1 具有抑制活性。这些数据代表了高度氧化的香豆素的一个新条目，其抗病毒活性可能基于细胞内氧化还原值的控制。
