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The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]

Chemistry of Heterocyclic Compounds volume 58, pages 462–472 (2022)Cite this article

A method for a regio- and stereoselective synthesis of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines] in 52–85% yields based on the three-component reaction of 3-nitro-2-trifluoromethyl-2H-chromenes with azomethine ylides generated in situ from benzylamines and indeno[1,2-b]quinoxalin-11-one by heating under reflux in CH2Cl2 for 2 h in the presence of 0.1 equiv of pyrrolidine was developed. The resulting compounds exhibited moderate cytotoxic activity against HeLa human cervical carcinoma cells in the concentration range of 10–5–10–4 M.

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Acknowledgment

This work was supported financially by the Russian Foundation for Basic Research (project no. 20-03-00716) within the framework of the State assignment of the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2020-0052).

The authors are grateful to the staff of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds” of the Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences for help in conducting physicochemical studies.

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    Savelii V. Barkovskii, Maria V. Ulitko, Alexey Yu. Barkov, Ivan А. Kochnev, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev & Vyacheslav Ya. Sosnovskikh

  2. A. M. Butlerov Institute of Chemistry, Kazan Federal University, 29/1 Kremlevskaya St., Kazan, 420008, Russia

    Roman А. Stepanyuk & Timur I. Madzhidov

Authors
  1. Savelii V. Barkovskii
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  2. Maria V. Ulitko
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  3. Alexey Yu. Barkov
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  4. Ivan А. Kochnev
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  5. Nikolay S. Zimnitskiy
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  6. Vladislav Yu. Korotaev
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  7. Vyacheslav Ya. Sosnovskikh
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  8. Roman А. Stepanyuk
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  9. Timur I. Madzhidov
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Corresponding authors

Correspondence to Vladislav Yu. Korotaev or Timur I. Madzhidov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(8/9), 462–472

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Barkovskii, S.V., Ulitko, M.V., Barkov, A.Y. et al. The synthesis and cytotoxic activity of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro[chromeno[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]. Chem Heterocycl Comp 58, 462–472 (2022). https://doi.org/10.1007/s10593-022-03113-7

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Keywords

  • azomethine ylides
  • benzylamines
  • indeno[1,2-b]quinoxalin-11-one
  • 3-nitro-2-trifluoromethyl-2H-chromenes
  • spiro[chromeno-[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines]
  • cytotoxic activity
  • 1,3-dipolar cycloaddition
  • in silico modeling