Studies on 3-Substituted 1, 2-Benzisoxazole Derivatives. VII. Catalytic Reduction of 3-Sulfamoylmethyl-1, 2-benzisoxazole and Reactions of the Resulting Products

doi:10.1248/CPB.30.333

Paper

Studies on 3-Substituted 1, 2-Benzisoxazole Derivatives. VII. Catalytic Reduction of 3-Sulfamoylmethyl-1, 2-benzisoxazole and Reactions of the Resulting Products

Published Jan 25, 1982 · H. Uno, M. Kurokawa

Chemical & Pharmaceutical Bulletin

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Abstract

Hydrogenation of 3-sulfamoylmethyl-1, 2-benzisoxazole (1) gave ω-sulfamoyl-2-hydroxyacetophenone (3) and its imide (2). Treatment of 3 with acid afforded a new route to 1, 2-benzoxathiin-4 (3H)-one-2, 2-dioxide (5). The oxime of 3 (4) was recyclized to provide 1, 2-benzisoxazole derivatives by treatment with acid or base. On pyrolysis 4 gave benzoxazole derivatives.

Study Snapshot

Hydrogenation of 3-sulfamoylmethyl-1, 2-benzisoxazole yields -sulfamoyl-2-hydroxyacetophenone, which can be converted into 1, 2-benzoxathiin-4 (3H)-one-2, 2-dioxide, and

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Studies on 3-Substituted 1, 2-Benzisoxazole Derivatives. VII. Catalytic Reduction of 3-Sulfamoylmethyl-1, 2-benzisoxazole and Reactions of the Resulting Products

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References

Citations

Design, Synthesis, and Evaluation of Novel Benzo[d]isoxazole Derivatives as Anticonvulsants by Selectively Blocking the Voltage-Gated Sodium Channel NaV1.1.

Novel benzo[d]isoxazole derivatives show anticonvulsant activity by selectively blocking voltage-gated sodium channel NaV1.1, offering potential for developing new selective NaV1.1 channel blockers as antiseizure drugs.

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

1,2-benzoxathiin-4(3H)-one 2,2-dioxide has high synthetic and pharmacological potential, but its synthesis, chemical transformations, and pharmacological activity require further research.

Photoredox-Catalyzed Generation of Sulfamyl Radicals: Sulfonamidation of Enol Silyl Ether with Chlorosulfonamide.

Photoredox-catalyzed generation of sulfamyl radicals enables efficient and convenient synthesis of antiseizure drug Zonisamide under mild and economic conditions.

Substituent effect on the reductive N-dearylation of 3-(indol-1-yl)-1,2-benzisoxazoles by rat liver microsomes.

Electron-withdrawing substituents on the benzisoxazole ring and indole ring significantly increase the rate of substrate reduction by rat liver microsomes, suggesting initial electron transfer is rate-determining.

Formation of 2-sulphamoylacetylphenol from zonisamide under aerobic conditions in rat liver microsomes.

Zonisamide is metabolized to SMAP in rat liver microsomes under both aerobic and anaerobic conditions by a cytochrome P450 belonging to the 3A subfamily.

Reductive metabolism of the anticonvulsant agent zonisamide, a 1,2-benzisoxazole derivative

Zonisamide's reductive metabolism in vitro is primarily mediated by microsomal cytochrome P-450, with soluble fractions enhancing reduction when combined with microsomal fractions.

Identification of rat urinary metabolites of zonisamide by TLC/SIMS.

Zonisamide is converted to three metabolites in rat urine, N-acetyl-3-sulfamoylmethyl-1, 2-benzisoxazole, 1, 2-benzisoxazoel-3-carboxylic acid, and the sulfate of (2-hydroxy