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Synthesis and antinociceptive activity of nitriles, esters, and amides of 2-amino-1-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-oxo-5-(2-oxo-2-arylethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylic acids

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Abstract

Synthesis of nitriles, esters, amides of the substituted 2-amino-1-(4,5,6,7-tetra-hydrobenzo[b]thiophen-2-yl)-4-oxo-5-(2-oxo-2-arylethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylic acids bearing the nitrile group at the thiophene ring by the reaction of the substituted 3-(3-cyanothiophen-2-yl)iminofuran-2(3H)-ones with the appropriate cyanoacetic acid derivatives was developed. The synthesized compounds demonstrated pronounced antinociceptive activity and low toxicity (toxicity class V of practically nontoxic substances).

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Authors and Affiliations

  1. Perm State National Research University, 15 ul. Bukireva, 614990, Perm, Russian Federation

    D. V. Lipin, K. Y. Parkhoma, V. M. Shadrin, R. R. Makhmudov & S. A. Shipilovskikh

  2. Perm National Research Polytechnic University, 29 Komsomolsky prosp., 614990, Perm, Russian Federation

    D. A. Shipilovskikh

  3. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    P. S. Silaichev

  4. School of Physics and Engineering, University ITMO, Build. A, 49 Kronverksky prosp., 197101, St. Petersburg, Russian Federation

    S. A. Shipilovskikh

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  1. D. V. Lipin
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Correspondence to S. A. Shipilovskikh.

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Additional information

This study was performed under financial support of the “Rational Use of the Earth Interior” Perm Scientific Educational Center 2023.

The experiments involving animals were performed in accordance with all applicable international, national, and institutional guidelines for the care and use of the laboratory animals.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1913–1920, August, 2023.

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Lipin, D.V., Parkhoma, K.Y., Shadrin, V.M. et al. Synthesis and antinociceptive activity of nitriles, esters, and amides of 2-amino-1-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-oxo-5-(2-oxo-2-arylethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylic acids. Russ Chem Bull 72, 1913–1920 (2023). https://doi.org/10.1007/s11172-023-3976-x

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