Synthesis and search for compounds with hemostatic activity in the series of 4-(het)aryl-4-oxobut-2-enoic acid derivatives

Пулина, Н. А.; Kozhukhar, V. Yu.; Kuznetsov, A.; Рубцов, А. Е.; Старкова, А. В.

doi:10.1007/s11172-017-1914-5

Cited by 12 publications

(3 citation statements)

References 17 publications

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“…1 Н NMR spectrum (400 MHz, CDCl 3 ), δ, ppm: 1.10 s (9Н, t-Bu), 5.52 s (2Н, СН 2 ), 5.54 s (1Н, СН), 7. 24 When conducting experiments on animals, the rules of laboratory practices and the requirements of ethics were observed.…”

Section: -Nitrobenzyl 2-[2-(diphenylmethylene)hydrazinyl]-55-dimethyl-4-oxohex-2-enoate (2o)mentioning

confidence: 99%

“…It is important to note that the moiety of 2,4-dioxobutanoic acid, which persists in the structure of imino-and hydrazonofuranones conversion products, is a signifi cant pharmacophore fragment that confi rms the inexhaustible interest in the fi eld of medicinal chemistry. The derivatives of 2,4-dioxobutanoic acids have a range of biological activity, such as hemostatic [24], redox [25], antimicrobial [26,27], including against multi-resistant strains [28], antiviral [29][30][31][32][33][34][35][36][37][38][39][40][41][42], antifungal [43], analgesic [44], anti-infl ammatory [45], reparation with respect to damaged DNA sites [46], inhibiting proteintithosinphospotases [47] associated with many diseases, including cancer, diabetes, and autoimmune processes. All this makes this type of structure promising for synthesis and learning.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: -Nitrobenzyl 2-[2-(diphenylmethylene)hydrazinyl]-55-dimethyl-4-oxohex-2-enoate (2o)mentioning

confidence: 99%

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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“…Как известно, N замещенные гидразиды 4 оксобут 2 еновых кислот, имеющие различные фармакофоры, в том числе адамантил, проявляют высокое био логическое действие при низкой острой ток сичности [2,3]. Для повышения биологической доступности и расширения спектра фармако логических испытаний нами впервые предло жен способ получения водорастворимых 4 (гет)арил 2 {2 [2 (адамантан 1 ил) 2 оксоэтили ден]гидразинил} 4 оксобут 2 еноатов натрия, обладающих высокой гемостатической и про тивомикробной активностью [4,5]. Однако анальгетическая и противовоспалительная ак тивность данных соединений ранее не изуча лась.…”

Section: Introductionunclassified

Studying of analgesic and anti-inflammatory activity of 2,4-dioxobutanoic acid hydrazine derivatives

et al. 2020

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Objective. To study the analgesic and anti-inflammatory activity of water-soluble hydrazine derivatives of 2,4-dioxobutanoic acids, as well as to determine the relationship between the structure of substances and their biological effects. Materials and methods. The laboratory synthesis methods were applied to obtain 2-hydrazine derivatives of 2,4-dioxobutanoic acids. The compounds were tested for biological activity using a hot plate test in mice and an acute inflammatory reaction caused by carrageenan-induced paw edema in rats. Results. The analgesic activity of four compounds is comparable to that of nimesulide. One of the substances obtained is found to exhibit higher anti-inflammatory activity than nimesulide during the 1st and 3rd hours of the experiment. Two compounds with a combination of high analgesic and anti-inflammatory activity were identified. The effect of certain radicals in the structure of the substances on the activities studied was discovered. Conclusions. The revealed relationship between the structure of original compounds and their biological activities can be used in the further synthesis and search for new domestic pharmaceutical substances with investigated effects.

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Reactions of 4-aryl-N-hetaryl-2-hydroxy-4-oxobut-2-enamides with hydroxylamine and biological activity of the products

et al. 2019

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Synthesis and search for compounds with hemostatic activity in the series of 4-(het)aryl-4-oxobut-2-enoic acid derivatives

Cited by 12 publications

References 17 publications

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

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

Studying of analgesic and anti-inflammatory activity of 2,4-dioxobutanoic acid hydrazine derivatives

Reactions of 4-aryl-N-hetaryl-2-hydroxy-4-oxobut-2-enamides with hydroxylamine and biological activity of the products

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