Synthesis and Properties of Alkyl
2-[2-(Diarylmethylidene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

Сюткина, А. И.; Игидов, Н. М.; Kizimova, I. A.

doi:10.1134/s1070428020040132

Cited by 7 publications

(3 citation statements)

References 20 publications

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“…Such a universal structural fragment can be found among the 3-imino-(hydrazinylidene)-furan-2(3H)-one derivatives, which results from their chemical availability due to the scalability of the synthetic methods [8] and the reactivity [9][10][11][12][13][14][15]. For example, the reactions of 3-imino-(hydrazinylidene)-furan-2(3H)-ones derivatives with various nucleophilic reagents lead to the attack on the carbonyl group of the lactone fragment and to the for-mation of acyclic or heterocyclic structures [16][17][18][19][20][21] that retain the pharmacophore fragment of 2,4-dioxobutanoic acid [22][23][24][25][26][27][28][29][30][31][32]. This fragment was found in the structure of various biologically active and natural compounds [33,34], which indicates that this idea is worth developing.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

et al. 2022

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New methyl 5-aryl-1-(furan-2-carbonyl)-1H-pyrazole-3-carboxylates were obtained via decyclization reaction of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides under the action of methanol. Starting N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides were obtained by intramolecular cyclization of substituted 4-aryl-2-[2-(furan-2-ylcarbonyl)hydrazinylidene]-4-oxobutanoic acids in propionic anhydride. The structure of the compounds obtained was confirmed by the 1H NMR spectroscopy, IR spectrometry and elemental analysis methods. Analgesic activity of some obtained compounds was studied by the “hot plate” method on outbred white mice of both sexes with intraperitoneal injection.

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Section: Introductionmentioning

confidence: 99%

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

et al. 2022

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“…We have previously shown [48] that, when heated 3-[(diarylmethylene)hydrazono]furan-2(3H)-ones 1a, 1b with primary and secondary aliphatic alcohols in the presence of triethylamine, the decyclization reaction to the formation of alkyl 2-[(diarylmethylene)hydrazono]-5,5-dimethyl-4-oxohexanoates 2a-2i proceeded with high yields up to 98% (Scheme 1). The interaction with tertiary aliphatic alcohols did not proceed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of Substituted 2-[2-(Diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

et al. 2021

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The synthesis of new substituted 2-[2-(diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates is described. The synthesis from commercially available starting materials included the preparation of 5,5-dimethyl-2,4-dioxohexanoic acid via Claisen condensation of 3,3-dimethylbutan-2-one (pinacolone) and diethyl oxalate in the presence of sodium methanolate. The resulting acid reacted with (diphenylmethylene)hydrazine to form 2-[(diphenylmethylene)hydrazono]-5,5-dimethyl-4-oxohexanoic acid. The initial 5-(tert-butyl)-3-[(diphenylmethylene)hydrazono]furan-2(3H)-one was obtained by a known literary method: intramolecular cyclisation of 2-[(diphenylmethylene)hydrazono]-5,5-dimethyl-4-oxohexanoic acid under the action of propionic anhydride. 5-(tert-Butyl)-3-[(diphenylmethylene)hydrazono]furan-2(3H)-one entered the decyclization reaction under the action of primary aromatic alcohols to form substituted 2-[2-(diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates. The presence of equimolar quantities of triethylamine was important; otherwise, the reaction proceeded with low yields. The isolation of target compounds was carried out by fi ltration of the resulting sediment followed by recrystallization. The structure of the compounds obtained was confi rmed by the 1 H and 13 C NMR spectroscopy methods. The resulting substituted esters exist in a solution of deuterated chloroform in one tautomeric form, in contrast to the previously studied solutions of deuterated DMSO, where up to four tautomeric forms were observed. Analgesic and anti-infl ammatory activity of new and previously synthesized compounds of this series has been studied. Analgesic activity was evaluated by the "Hot Plate" test on outbred white mice of both sexes with intraperitoneal injection. Anti-infl ammatory activity was studied on a carrageenan-induced paw edema model with oral administration of the studied substances. One compound possesses both high analgesic and high anti-infl ammatory effects, which causes the prospects for its use as a pharmacologically active substance.

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“…The synthesis of substituted Gewald aminothiophenes can be carried out using the Gewald reaction [7][8][9]. In turn, 3imino(hydrazono)-3H-furan-2-ones have high reactivity, leading to the production of compounds of various structures [10][11][12][13][14][15][16][17]. Decyclization reactions of 3-imino-3Hfuran-2-ones lead to the production of 2,4-dioxobutanoic acid derivatives, for which antiviral [18][19][20][21][22], analgesic [23], anti-inflammatory [24], antimicrobial [25] activity was determined.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

2021

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The synthesis of new derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid is described. Starting 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids were obtained by intramolecular cyclisation of substituted 4-aryl-4-oxo-2-thienylaminobut-2-enoic acids in acetic anhydride. New derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acids were obtained via decyclization reaction of 2-{[5-aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acids. The structure of the compounds obtained was confirmed by the 1H and 13C NMR spectroscopy, IR spectrometry and elemental analysis methods. Analgesic activity of new compounds has been studied by the “hot plate” method on outbred white mice of both sexes with intraperitoneal injection. It was found that derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid possess analgesic effect exceeding the effect of the comparison drug metamizole.

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Synthesis and Properties of Alkyl 2-[2-(Diarylmethylidene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

Cited by 7 publications

References 20 publications

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

Synthesis and Biological Activity of Substituted 2-[2-(Diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

Synthesis and analgesic activity evaluation of derivatives of 2-[(1,4-dioxo-1-amino-4-arylbutyl-2-en-2-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

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