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Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities

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  • Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities

    J Nat Prod. 2017 Dec 13. doi: 10.1021/acs.jnatprod.7b00665. [Epub ahead of print]
    Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities.

    Bizzarri BM1, Botta L1, Capecchi E1, Celestino I2, Checconi P3, Palamara AT2,3, Nencioni L3, Saladino R1.
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    Abstract

    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.


    PMID: 29236486 DOI: 10.1021/acs.jnatprod.7b00665
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