Mechanism of Decomposition of Cyclic Peroxides, 4-Alkoxy-1,4-dihydro-2,3-benzodioxin-1-ols, to Afford Hydroxyl Radical

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The decomposition of 4-alkoxy-1,4-dihydro-2,3-benzodioxin-1-ols (1,Bd) in aqueous media was examined. Increasing the water content of the medium accelerated the decomposition of 1 and increased the formation of the corresponding 2-formyl benzoic acid ester (2) as the decomposition product. Electron spin resonance (ESR) studies using dimethylpyrroline N-oxide (DMPO) as a spin trapping reagent had revealed that bydroxyl radicals are formed during the decomposition of 1 (Matsugo et al., FEBS Lett., 184,25 (1985)). Thus, water-mediated decomposition of 1 was suggested to occur, affording the ester 2 and hydroxyl radical. Direct involvement of water was confirmed by an ^<18>O isotopic tracer experiment which revealed that ^<18>O was incorporated exclusively into the formyl position of the ester 2. It is plausible that a hydrated hydroperoxide (5) is formed by the addition of water at the formyl position of the ring-opened structure of 1 at the initial stage fo the decomposition of 1. Preliminary studies on the antibacterial activities of 1 showed moderate cell-killing activity, especially to Pseudomonas strains, and the activity was found to be related to the decomposition of 1.
公益社団法人日本薬学会の論文
1991-03-25