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

Игорь Б. Кутяшев, Мария В. Улитко, Алексей Ю. Барков, Николай С. Зимницкий, Владислав Ю. Коротаев, Вячеслав Я. Сосновских
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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


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

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