The oxidized products of 8-methoxypsoralen (8-MOP) with H2O2-NaOCl

Article abstract of DOI:10.1248/cpb.39.2715

In order to obtain adducts of 8-methoxypsoralen (8-MOP, 1) and singlet oxygen (¹O₂), the oxidation of 1 with chemically generated singlet oxygenin H₂O₂ -NaOCl was undertaken. Bioassay-directed fractionation of the crude oxidized products has led to the isolation and characterization of a novel derivative of 1, 2,3-dihydro-2,9-dimethoxy-3-hydroxy-7H-furo[3,2-g][1]benzopyran-7-one (2) as a substance inhibiting chemotactic activity of polymorphonuclear neutrophils toward anaphylatoxin C5(a) des Arg. The structure of 2 was determined from the spectroscopic data and by correlation with its acetate (2a). Furthermore, the oxidation of 1 in H₂O₂-NaOCl afforded 5-chloro-9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one (3) and 6-formyl-7-hydroxy-8-methoxy-2H-1-benzopyran-2-one (4) along with 1, but they exhibited no such activity.

Full text of DOI:10.1248/cpb.39.2715

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