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Synthesis, intramolecular cyclization, and antinociceptive activity of 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids

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Abstract

Synthesis and intramolecular cyclization of the substituted 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids were studied. It was found that the synthesized compounds underwent the intramolecular cyclization to give the substituted ethyl 4-(4-chlorophenyl)-2-{[2-oxofuran-3(2H)-ylidene]-amino}thiophene-3-carboxylates. Evaluation of the biological activity of the synthesized compounds showed that they have pronounced antinociceptive activity along with low toxicity.

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Authors and Affiliations

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

    I. A. Gorbunova, I. P. Nikonov, R. R. Makhmudov, P. S. Silaichev & S. A. Shipilovskikh

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

    D. A. Shipilovskikh

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

    S. A. Shipilovskikh

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Correspondence to S. A. Shipilovskikh.

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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 Scientifi c 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”.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2255–2262, September, 2023.

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Gorbunova, I.A., Nikonov, I.P., Makhmudov, R.R. et al. Synthesis, intramolecular cyclization, and antinociceptive activity of 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids. Russ Chem Bull 72, 2255–2262 (2023). https://doi.org/10.1007/s11172-023-4023-7

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