Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoyl hydrazones of aromatic aldehydes

Лебедев, А. А.; Смирнов, В. А.; Posokhov, V. P.; Simerzina, L. V.

doi:10.1007/bf00763662

Pharm Chem J

1988

DOI: 10.1007/bf00763662

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Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoyl hydrazones of aromatic aldehydes

А. А. Лебедев¹,

В. А. Смирнов²,

V. P. Posokhov³

et al.

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1997

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“…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.…”

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Syntheses of drug on the basis of 3-sulfamoyl-4-chlorobenzoylazide. Diuretic activity of 3-sulfamoyl-4-chlorobenzoic acid amides

Смирнов

Simerzina

1997

Pharm Chem J

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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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confidence: 99%

Syntheses of drug on the basis of 3-sulfamoyl-4-chlorobenzoylazide. Diuretic activity of 3-sulfamoyl-4-chlorobenzoic acid amides

Смирнов

Simerzina

1997

Pharm Chem J

Self Cite

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Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoyl hydrazones of aromatic aldehydes

Cited by 1 publication

References 2 publications

Syntheses of drug on the basis of 3-sulfamoyl-4-chlorobenzoylazide. Diuretic activity of 3-sulfamoyl-4-chlorobenzoic acid amides

Syntheses of drug on the basis of 3-sulfamoyl-4-chlorobenzoylazide. Diuretic activity of 3-sulfamoyl-4-chlorobenzoic acid amides

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