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.
Bizzarri, B.m., Botta, L., Capecchi, E., Celestino, I., Checconi, P., Palamara, A.t., et al. (2017). Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities. JOURNAL OF NATURAL PRODUCTS, 80(12), 3247-3254 [10.1021/acs.jnatprod.7b00665].
Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities
Botta L.;
2017-01-01
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
