Synthesis and diuretic activity of phenoxyacetic acid and anisole derivatives

Лебедев, А. А.; Смирнов, В. А.; Bazhmina, M. Yu.; Karpacheva, T. A.

doi:10.1007/bf00770446

Cited by 2 publications

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“…The effect of compounds III-VIII on diuresis, natriuresis, and kaliuresis was studied on intact white rats weighing 200-300 g as described in [2,4]. Total diuresis and the excretion of sodium and potassium ions were determined 4 h after the beginning of experiment.…”

Section: Experimental Pharmacological Partmentioning

confidence: 99%

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Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoylhydrazones of 4-acetylphenoxyacetic acid and its derivatives

Смирнов

Simerzina

1997

Pharm Chem J

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Earlier we reported [1] that 3-sulfamoyl-4-chlorobenzoylhydrazones of some aromatic aldehydes exhibited diuretic and saluretic activity, although the effect could be observed only for a rather short time. This behavior could be attributed to the fact that these hydrazones are rapidly hydrolyzed in the organism with the formation of a 3-sulfamoyl-4-chlorobenzoic acid hydrazide (I), capable of producing weak diuretic action, and the corresponding carbonyl compounds possessing no diuretic properties.It was therefore of interest to synthesize and study 3-sulfamoyl-4-chlorobenzoylhydrazones of carbonyl compounds that would exhibit diuretic activity by themselves. We have succeeded in finding such compounds among the derivatives of 4-acetylphenoxyacetic acid [2].The initial hydrazide I was synthesized by heating a mixture of 3-sulfamoyl-4-chlorobenzoic acid ethyl ester (II) and hydrazine hydrate for 10 min at 70 -75~ in the absence of solvent. This reaction gives a target product of higher purity and provides a higher yield as compared to the method described in [3]. 3-Sulfamoyl-4-chlorobenzoylhydrazones of4-acetylphenoxyacetic acid and its derivatives (III-VIII) were obtained by the condensation reaction between hydrazide I and the corresponding carbonyl compounds in a 2-propanol medium in the presence of a catalytic amount of acetic acid. The proposed structures of compounds III-VIII were confirmed by data of elemental analyses (corresponding to I Samara State Medical University, Samara, Russia. 543 the empirical formulas) and the results of UV, IR, and IH NMR spectroscopic measurements. The UV spectra of III-VIII exhibit two absorption maxima: at 285 -300 and 328 -349 nm. The IR spectra of compounds III-VIII display the following characteristic absorption bands (cm-l): 3370-3435, 3305-3360, 3185-3215 (N-H in SO2NH2 and CONH), and 1710-1725 (COOR'). The IH NMR spectra of III-VIII contain signals at 8 = 11.04 -11.30 ppm attributed to protons of the CONHN=C group. EXPERIMENTAL CHEMICAL PARTThe IR spectra were measured on a Specord M-80 spectrophotometer using samples pelletized with KBr. The IH NMR spectra were recorded on a Bruker W-80 spectrometer (working frequency, 80 MHz) using DMSO-d6 as the solvent and HMDS as the internal standard. The UV spectra were measured on a SF-26 spectrophotometer in acetonitrile solutions.3-Sulfamoyl-4-ehlorobenzoie acid hydrazide (I). A mixture of 26.4 g (0.1 mole) of compound II and 40 g (0.8 mole) of hydrazine hydrate was heated to 70~ treated for 10 min at 70 -75~ and cooled to room temperature. To this mixture was added 150 ml of water and then glacial acetic acid to pH 7.5. Finally, the reaction mixture was cooled to 0~ and the precipitate was filtered, washed with 300 ml of water, and dried at I05~ to obtain 23.0-23.5 g (92-94%) of a white product; m.p., 216-218~Crystallization from water gives 4.6 g of the product per 100 ml water (yield, 75 -80%) 3-Sulfamoyl--4-chlorobenzoylhydrazones (Ill-VIII). To a hot solution of 2.5 g (10 mmole) of compound I in 40 ml

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Section: Experimental Pharmacological Partmentioning

confidence: 99%

“…We have succeeded in finding such compounds among the derivatives of 4-acetylphenoxyacetic acid [2].…”

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confidence: 96%

Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoylhydrazones of 4-acetylphenoxyacetic acid and its derivatives

Смирнов

Simerzina

1997

Pharm Chem J

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“…The diuretic and natriuretic activity of compounds V--: XIV were studied on white rats using the methods described in [31,32].…”

Section: Experimental Pharmacological Partmentioning

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

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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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Synthesis and diuretic activity of phenoxyacetic acid and anisole derivatives

Cited by 2 publications

References 4 publications

Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoylhydrazones of 4-acetylphenoxyacetic acid and its derivatives

Synthesis and diuretic activity of 3-sulfamoyl-4-chlorobenzoylhydrazones of 4-acetylphenoxyacetic acid and its derivatives

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

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