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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]

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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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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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).

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  • 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