THE SYNTHESIS AND CYTOTOXIC ACTIVITY OF <i>N</i>-UNSUBSTITUTED 3-ARYL-4-(TRIFLUOROMETHYL)-4<i>H</i>-SPIRO[CHROMENO[3,4-<i>c</i>]PYRROLIDINE-1,11'-INDENO[1,2-<i>b</i>]QUINOXALINES]

Authors

  • Савелий В. Барковский 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
  • Мария В. Улитко 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
  • Алексей Ю. Барков 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
  • Иван А. Кочнев 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
  • Николай С. Зимницкий 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
  • Владислав Ю. Коротаев 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
  • Вячеслав Я. Сосновских 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
  • Роман А. Степанюк A. M. Butlerov Institute of Chemistry, Kazan Federal University, 29/1 Kremlevskaya St., Kazan 420008
  • Тимур И. Маджидов A. M. Butlerov Institute of Chemistry, Kazan Federal University, 29/1 Kremlevskaya St., Kazan 420008

DOI:

https://doi.org/10.1007/6907

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

Abstract

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 th/e concentration range of 10–5–10–4 M.

Authors: Savelii V. Barkovskii, Maria V. Ulitko, Alexey Yu. Barkov, Ivan А. Kochnev, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev1*, Vyacheslav Ya. Sosnovskikh, Roman А. Stepanyuk, Timur I. Madzhidov*

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Published

2022-09-22

Issue

Vol. 58 No. 8/9 (2022)

Section

Original Papers