REGIO- AND STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE YLIDES BASED ON ISATINS AND (THIA)PROLINE TO 3-NITRO-2-(TRIFLUORO(TRICHLORO)METHYL)-2<i>H</i>-CHROMENES: SYNTHESIS AND CYTOTOXIC ACTIVITY OF 6'-(TRIHALOMETHYL)SPIRO[CHROMENO(THIA)PYRROLIZIDINE-11,3'-INDOLIN]-2'-ONES

Authors

  • Игорь Б. Кутяшев Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000
  • Мария В. Улитко Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000
  • Алексей Ю. Барков Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000
  • Николай С. Зимницкий Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000
  • Владислав Ю. Коротаев Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000
  • Вячеслав Я. Сосновских Institute of Natural Sciences and Mathematics of Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000

DOI:

https://doi.org/10.1007/6321

Keywords:

azomethine ylide, isatins, 3-nitro-2-(trihalomethyl)-2H-chromene, L-proline, spiro[chromeno(thia)oxindole-pyrrolizidines], L-thiaproline, cytotoxic activity, 1, 3-dipolar cycloaddition

Abstract

A regio- and stereoselective method for the synthesis of (trifluoro(trichloro)methyl)-substituted spiro[chromeno(thia)oxindole-pyrrolizidines] in 53–97% yields was developed on the basis of the three-component reaction of 3-nitro-2-(trifluoro(trichloro)methyl)-2H-chromenes with azomethine ylides generated in situ from isatins and L-(thia)proline in EtOH at 30°C. The obtained compounds demonstrated high cytotoxic activity against HeLa human cervical cancer and RD human embryonic rhabdomyosarcoma cells.

Authors: Igor B. Kutyashev, Maria V. Ulitko, Alexey Yu. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev*, Vyacheslav Ya. Sosnovskikh

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Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers