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An analysis of data available in the literature on the diuretic properties of 3-sulfamoyl-4-chlorobenzoic acid amides [ 1 -12] and hydrazides [ 13 -29] suggests that a condition necessary for the diuretic activity of these compounds consists in the presence ofa-CO-NH-fragment in the meta position with respect to the sulfamoyl group. In particular, Lebedev et al. [30] showed that the diuretic and natriuretic activity of 3-sulfamoyl-4-chlorobenzoylhydrazones of aromatic aldehydes depend on the polarity of N-H bonds in this fragment.It was therefore of interest to study the diuretic activity of compounds in which, first, the distance of hydrogen atom in the -CO-NH-group from the benzene ring containing the sulfamoyl group differs from the corresponding values in 3-sulfamoyl-4-chlorobenzoyl acid amides, hydrazides, and hydrazones and, second, the character of the electronic influence of substituents on the N-H bond differs from that in 3-sulfamoyl-4-chlorobenzoylhydrazones of aromatic aldehydes.For this purpose, we have synthesized a series of N-(3-sulfamoyl-4-chlorophenyl)carbamates, N-(3-sulfamoyl-4-chlorophenyl)-N'-R-ureas, and 3-sulfamoyl-4-chlorobenzoic acid amides and characterized their diuretic activity. The compounds were synthesized proceeding from 3-sulfamoyl-4-chlorobenzoylazide (II) according to the scheme.The initial azide II was obtained with high yield (94-96%) by a reaction between 3-sulfamoyl-4-chlorobenzoic. acid hydrazide (I) and sodium nitrite in a hydrochloric medium. The structure of compound II was confirmed by data of the elemental analyses and by the synthesis of two known 3-sulfamoyl-4-chlorobenzoyl acid amides (VIII, IX) [5] on the basis of azide II.The synthesis of 3-sulfamoyl-4-chlorobenzoyl acid amides (VIII-XIV) was conducted by two pathways. First, by

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1998sulfonamides sulfonamides (hydrazides, ureides) (benzene compounds) Q 0560 -082Syntheses on the Basis of 3-Sulfamoyl-4-chlorobenzoyl Azide. Diuretic Activity of 3-Sulfamoyl-4-chlorobenzoylamides.-A number of amides [cf. (X)], carbamates [cf. (IV)] and urea derivatives [cf. (VII)] of 3-sulfamoyl-4-chlorobenzoic acid is synthesized from the corresponding azide (II) and evaluated for their diuretic activity. Only the amide derivatives exhibit significant activity. -(SMIRNOV, V. A.; SIMERZINA, L. V.; Khim.-Farm.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.