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,Chemistry of Heterocyclic Compounds

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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
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2021-09-08 , DOI: 10.1007/s10593-021-02979-3
Igor B. Kutyashev ₁ , Maria V. Ulitko ₁ , Alexey Yu. Barkov ₁ , Nikolay S. Zimnitskiy ₁ , Vladislav Yu. Korotaev ₁ , Vyacheslav Ya. Sosnovskikh ₁

Affiliation

A regio- and stereoselective method for the synthesis of (trifluoro(trichloro)methyl)-substituted spiro[chromeno(thia)pyrrolizidineoxindoles] in 53–97% yields was developed on the basis of the three-component reaction of 3-nitro-2-(trifluoro(trichloro)methyl)-2Hchromenes 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.

中文翻译：

基于靛红和 (thia) 脯氨酸的 Azomethine Ylides 的区域和立体选择性 1,3-偶极环加成反应到 3-nitro-2-(trifluoro(trichloro)methyl)-2H-chromenes：6-(trihalomethyl) 的合成和细胞毒活性-spiro[chromeno(thia)pyrrolizidine-11,3'-indolin]-2'-ones

基于 3-硝基-2 的三组分反应，开发了一种区域和立体选择性方法，用于合成（三氟（三氯）甲基）取代的螺[色基（硫杂）吡咯并二吲哚]，产率为 53-97%。 -（三氟（三氯）甲基）-2 H色烯与偶氮甲碱叶立德在 30°C 的乙醇中由靛红和 L-（硫杂）脯氨酸原位生成。获得的化合物对 HeLa 人宫颈癌和 RD 人胚胎横纹肌肉瘤细胞显示出高细胞毒活性。

更新日期：2021-09-09

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