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Synthesis, Intramolecular Cyclization, and Analgesic Activity of Substituted 2-[2-(Furancarbonyl)hydrazinylydene]-4-oxobutanoic Acids

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Abstract

A method was proposed for the synthesis of substituted 2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic acids by the reaction of 4-aryl-2,4-dioxobut-2-enoic acids with furan-2-carbohydrazide. It was found that substituted 2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic acids undergo intramolecular cyclization in the presence of propionic anhydride to form the corresponding substituted 2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic acids. The analgesic activity and acute toxicity of the obtained compounds were studied, it was found that the obtained compounds have a pronounced analgesic activity and low toxicity. According to the toxicity classification of drugs, the resulting substituted 2-[2-(furan-2-carbonyl)hydrazinylidene]-4-oxobutanoic acids and 2-[5-aryl-2-oxofuran-3(2H)-ylidene]furan-2-carbohydrazides belong to class V practically non-toxic drugs.

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Funding

This study was performed under financial support by the “Rational Use of the Earth Interior” Perm Scientific Educational Center, 2022. Tests of analgesic activity were carried out in the research laboratory of biologically active substances of the “Perm State National Research University.”

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, 614990, Perm, Russia

    S. N. Igidov, A.Yu. Turyshev & N. M. Igidov

  2. Merck LLC, 115054, Moscow, Russia

    S. N. Igidov

  3. Perm State University, 614990, Perm, Russia

    R. R. Makhmudov & S. A. Shipilovskikh

  4. Perm National Research Polytechnic University, 614990, Perm, Russia

    D. A. Shipilovskikh

  5. ITMO University, 197101, St. Petersburg, Russia

    S. A. Shipilovskikh

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  1. S. N. Igidov
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Correspondence to S. A. Shipilovskikh.

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Igidov, S.N., Turyshev, A., Makhmudov, R.R. et al. Synthesis, Intramolecular Cyclization, and Analgesic Activity of Substituted 2-[2-(Furancarbonyl)hydrazinylydene]-4-oxobutanoic Acids. Russ J Gen Chem 92, 1629–1636 (2022). https://doi.org/10.1134/S1070363222090067

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