Synthesis and Biological Activity of N-Aryl(alkyl)-2-[2-(9H-fluoren-9-ylidene)hydrazinylidene]-5,5-dimethyl-4-oxohexanamides

Сюткина, А. И.; Игидов, Н. М.; Дмитриев, М. В.; Махмудов, Р. Р.; Новикова, В. В.

doi:10.1134/s1070363219070065

Cited by 12 publications

(3 citation statements)

References 12 publications

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“…It was previously shown that 3-imino(hydrazono)-3Hfuran-2-ones can be decyclized under the action of aliphatic, aromatic, and heterocyclic amines to form amides of 4aryl(tert-butyl)-4-oxo-2-amino(hydrazono)-2-eno acids [26,27]. In this paper, synthesis and analgesic activity of…”

Section: Introductionmentioning

confidence: 90%

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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Section: Introductionmentioning

confidence: 90%

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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“…Fluorenone is a polysubstituted benzene derivative that plays a significant role in the fields of medicinal chemistry and materials sciences. Fluorenone scaffolds are extensively found in a variety of physiologically significant compounds including antinociceptive, 20 anticancer, 21 antimicrobial, 22 antitubercular, 23 and antiviral 24 compounds. For instance, fluorenone based hybrids III and IV with anticancer and antitubercular activity, respectively, are given in Fig.…”

Section: Introductionmentioning

confidence: 99%

Fluorenone–thiazolidine-4-one scaffolds as antidiabetic and antioxidant agents: design, synthesis, X-ray crystal structures, and binding and computational studies

Doddagaddavalli

Kalalbandi²,

Naik³

et al. 2023

New J. Chem.

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“…3-Imino(hydrazono)-3H-furan-2-ones are convenient initial compounds for the creation of new derivatives of the aroyl-and pivaloylpyruvic acids (APA and PPA) [1,2], as well as new heterocyclic systems [3][4][5][6][7]. Preparation of 3-imino(hydrazono)-3H-furan-2ones can be carried out both from the already existing furan cycle [8][9][10][11][12][13][14], and methods of intramolecular cyclization of 2-imino(hydrazono)-4-oxobutanoic acids [15][16][17][18][19]. 3-Imino(hydrazono)-3H-furan-2-ones have several reactive centers in its structure, due to which it becomes possible to change the direction of the attacking reagent, depending on the nature of the substituents in the furan cycle and imino(hydrazono)function.…”

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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Synthesis and Biological Activity of N-Aryl(alkyl)-2-[2-(9H-fluoren-9-ylidene)hydrazinylidene]-5,5-dimethyl-4-oxohexanamides

Cited by 12 publications

References 12 publications

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

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

Fluorenone–thiazolidine-4-one scaffolds as antidiabetic and antioxidant agents: design, synthesis, X-ray crystal structures, and binding and computational studies

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

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