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Synthesis and antinociceptive activity of N-substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]4-oxobut-2-enamides

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Abstract

N-Substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]-4-oxobut-2-enamides were synthesized by the reaction of 2-[(5-aryl-2-oxofuran-3(2H)-ylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitriles with primary amines. The synthesized compounds are non-toxic and have pronounced antinociceptive activity.

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Authors and Affiliations

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

    I. A. Gorbunova, E. A. Okoneshnikova, R. R. Makhmudov, D. A. Shipilovskikh, V. M. Shadrin, P. S. Silaichev & S. A. Shipilovskikh

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

    I. A. Gorbunova, E. A. Okoneshnikova & S. A. Shipilovskikh

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

    D. A. Shipilovskikh

  4. Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation, 101 ul. Ekaterininskaya, 614990, Perm, Russian Federation

    V. M. Shadrin

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  1. I. A. Gorbunova
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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.

All experiments involving animals and their maintenance complied the rules of European Convention for the Protection of Vertebrate Animals used for Experimental and Other Scientific Purposes (Strasbourg, 1986), the rules of Good Laboratory Practice, and the Order of the Ministry of Health of the Russian Federation dated June 6, 2003, No. 267 “On Approval of the Rules of Good Laboratory Practice”.

Based on the materials of the VI International conference “Modern Synthetic Methodologies for Creating Drugs and Functional Materials” (MOSM 2022) (November 7–11, 2022, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1905–1912, August, 2023.

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Gorbunova, I.A., Okoneshnikova, E.A., Makhmudov, R.R. et al. Synthesis and antinociceptive activity of N-substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]4-oxobut-2-enamides. Russ Chem Bull 72, 1905–1912 (2023). https://doi.org/10.1007/s11172-023-3975-y

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