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.

doi:10.1248/CPB.42.500

Paper

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.

Published Mar 15, 1994 · Y. Imakura, T. Konishi, K. Uchida

Chemical & pharmaceutical bulletin

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4

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Abstract

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 Ca2+ antagonistic activities were evaluated. Among these compounds, 2-(2-bromophenylthiomethoxy)-10-(2-diethylaminoacetyl)-3- methoxyphenothiazine (46) showed the most potent Ca2+ 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.

In Vitro Study

Study Snapshot

The cleavage reaction with sodium methoxide-thiols in dimethyl sulfoxide produces biologically active compounds, with 2-(2-bromophenylthiomethoxy)-10-(2-diethylaminoacetyl)-3-methoxyphenothia

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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.

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References

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The reaction of chlorpromazine with vanadate ion produces a red-colored chlorpromazine free radical and vanadyl ion, with implications for the pharmacological action of both compounds.

Citations

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Practical Synthesis of a Highly Functionalized Thiazole Ketone.

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