STUDIES ON 3-SUBSTITUTED 1,2-BENZISOXAZOLE DERIVATIVES .6. SYNTHESES OF 3-(SULFAMOYLMETHYL)-1,2-BENZISOXAZOLE DERIVATIVES AND THEIR ANTICONVULSANT ACTIVITIES

Several 3-(sulfamoylmethyl)-l, 2-benzisoxazole derivatives were synthesized from 3-(bromomethyl)-l, 2-benzisoxazole by the reaction with sodium bisulfite followed by chlorination and amination. Some of them displayed marked anticonvulsant activity in mice. The introduction of a halogen atom to the 5 position of the benzisoxazole ring caused increased activity and neurotoxicity; the substitution of a sulfamoyl group caused decreased activity. The activity of monoalkylated compounds might be the result of biotransformation. Among these compounds, 3-(sulfamoylmethyl)-l, 2-benzisoxazole (la) was thought to be the most promising as an anticonvulsant from the ratio of NTD50and ED50. © 1979, American Chemical Society. All rights reserved.