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2,3-Dihydrobenzofuran-2-carboxylic acids substituted with electronegative nitro, acyl and sulfamoyl groups at the 4-position were synthesized and tested for oral diuretic and saluretic activities in rats and mice. The intraperitoneal uricosuric activity was also tested by a clearance method using oxonate-treated rats. The 4-nitro compounds (11b, 12b, 13b and 14b) showed more potent saluretic activity than the corresponding 5-nitro compounds (7b, 18b, 19b and 20). Although the 5-acyl compounds were reported to show potent saluretic activities, the 4-acyl compounds (41a and b) had much lower activities. On the other hand, the saluretic activities of the 4-sulfamoyl compounds (22a-e) were as potent as those of the 5-sulfamoyl compounds reported previously. Uricosuric activity was found in 14b and 22a.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Studies on uricosuric diuretics. II. 6,7-Dichloro-4-nitro-, 6,7-dichloro-4-sulfamoyl- and 6,7-dichloro-4-acyl-2,3-dihydrobenzofuran-2-carboxylic acids.