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Regioselective cleavage reaction of the aromatic methylenedioxy ring. VI. Synthesis of phenothiazine analogues by using the cleavage reaction with sodium methoxide-thiols in dimethyl sulfoxide and evaluation of their biological activities



Regioselective cleavage reaction of the aromatic methylenedioxy ring. VI. Synthesis of phenothiazine analogues by using the cleavage reaction with sodium methoxide-thiols in dimethyl sulfoxide and evaluation of their biological activities



Chemical & Pharmaceutical Bulletin 42(3): 500-511



The reactions of aromatic methylenedioxy compounds containing electron-withdrawing groups with sodium methoxide-thiols in dimethyl sulfoxide gave 3- and 4-hydroxybenzene derivatives in good yield by regioselective attack of the thiolate ions on the methylenedioxy ring. The formation mechanism and the reactivity of thiolate ions in the cleavage reaction of the methylenedioxy ring are discussed. Various biologically active compounds, 32a, 32d, 36b, 38b, 41b and 44-47, were prepared from the 4-hydroxybenzene derivatives and their Ca-2+ antagonistic activities were evaluated. Among these compounds, 2-(2-bromophenylthiomethoxy)-10-(2-diethylaminoacetyl)-3-methoxyphenothiazine (46) showed the most, potent Ca-2+ antagonistic activity. Biological activity could be conveniently evaluated by measurement of the peak height of the vanadyl ion (+4 oxidation ion) signal produced by redox reaction between the phenothiazine derivatives and vanadate ion +5 oxidation ion) with ESR spectroscopy.

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Accession: 009318432

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PMID: 8004695

DOI: 10.1248/cpb.42.500


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