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Synthesis, analgesic and antimicrobial activity of substituted 2-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxo-4-phenylbut-2-enoates

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Abstract

New substituted 2-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxo-4-phenylbut-2-enoates were obtained by the reaction of 2-((2-oxo-5-phenylfuran-3(2H)-ylidene)-amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile with alcohols. The structures of the compounds obtained were confirmed by 1H and 13C NMR spectroscopy and elemental analysis. A number of new compounds were found to have a pronounced analgesic activity, as well as a weak antimicrobial effect or its absence.

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Authors and Affiliations

  1. Perm State National Research University, 15 ul. Bukireva, 614068, Perm, Russian Federation

    Yu. O. Sharavyeva, A. I. Siutkina, S. V. Chashchina, R. R. Makhmudov & S. A. Shipilovskikh

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

    A. I. Siutkina, S. V. Chashchina & V. V. Novikova

  3. Federal Scientific Center of Medical and Preventive Health Risks Management Technologies, 82 ul. Monastyrskaya, 614045, Perm, Russian Federation

    R. R. Makhmudov

  4. Faculty of Physics and Technology, National Research University ITMO, Lit. A, 49 Kronverkskii prosp., 197101, St. Petersburg, Russian Federation

    S. A. Shipilovskikh

Authors
  1. Yu. O. Sharavyeva
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  2. A. I. Siutkina
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  3. S. V. Chashchina
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Correspondence to A. I. Siutkina.

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The work was financially supported by the Perm “Rational Nature Management” Scientific and Educational Center for year 2021.

All experiments involving animals and their maintenance complied with the rules of laboratory practice as outlined in the European Convention for the Protection of Vertebrate Animals used for Experimental and other Scientific Purposes CETS 123 (Strasbourg, 1986), the Order of the Ministry of Health of the Russian Federation dated April 1, 2016, No. 199n “On Approval of the Rules of Good Laboratory Practice” (GLP) in compliance with the International Recommendations of the European Convention for the Protection of Vertebrate Animals used for Experimental Studies (1997).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 538–542, March, 2022.

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Sharavyeva, Y.O., Siutkina, A.I., Chashchina, S.V. et al. Synthesis, analgesic and antimicrobial activity of substituted 2-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxo-4-phenylbut-2-enoates. Russ Chem Bull 71, 538–542 (2022). https://doi.org/10.1007/s11172-022-3445-y

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