(2E)-3-(2-methyl-1H-indol-3-yl)-2-(methylsulfonyl)acrylonitrile | 1519005-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2E)-3-(2-methyl-1H-indol-3-yl)-2-(methylsulfonyl)acrylonitrile
• 英文别名: (E)-3-(2-methyl-1H-indol-3-yl)-2-methylsulfonylprop-2-enenitrile
• CAS: 1519005-14-1
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: FGZMLCWUDKSIMF-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 在 苯甲酰氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (2E)-3-(2-methyl-1H-indol-3-yl)-2-(methylsulfonyl)acrylonitrile
  参考文献：
  名称：

  通过亚胺盐与活性亚甲基试剂的原位缩合非常规立体选择性一锅合成Knoevenagel型吲哚

  摘要：

  描述了一种简单的一锅法，用于立体选择性合成Knoevenagel型吲哚。该方法基于在三乙胺存在下吲哚亚胺盐（已充分表征其中的四种）与无环对称和不对称活性亚甲基试剂的原位反应。总的来说，总产量是中等至良好。讨论了影响立体选择性的一些相关反应参数和空间效应。

  DOI：

  10.1016/j.tet.2013.10.086

文献信息

• Unconventional Knoevenagel-type indoles: Synthesis and cell-based studies for the identification of pro-apoptotic agents
  作者：Andrea Spallarossa、Chiara Caneva、Matteo Caviglia、Silvana Alfei、Stefania Butini、Giuseppe Campiani、Sandra Gemma、Margherita Brindisi、Daniela M. Zisterer、Sandra A. Bright、Clive D. Williams、Emmanuele Crespan、Giovanni Maga、Giuseppina Sanna、Ilenia Delogu、Gabriella Collu、Roberta Loddo

  DOI：10.1016/j.ejmech.2015.08.009

  日期：2015.9

  A new series of indole-based analogues were recently identified as potential anticancer agents. The Knoevenagel-type indoles herein presented were prepared via a one-pot condensation of iminium salts with active methylene reagents and were isolated as single geometric isomers. Biological evaluation in different cell-based assays revealed an antiproliferative activity for some analogues already in the nanomolar range against leukaemia, breast. and renal cancer cell lines. To explain these effects, the most promising analogues of the series were engaged in further cell-based studies. Compounds 5e, I, p and 6a, b highlighted a pro-apoptotic potential being able to induce apoptosis in HL60, K562 and MCF-7 cell lines in a dose and time-dependent manner. The ability of these compounds to arrest cell cycle at the G2/M phase inspired the immunofluorescence studies which allowed us to identify tubulin as a potential target for compounds 5l and 6b. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Unconventional stereoselective one-pot synthesis of Knoevenagel-type indoles via in situ condensation of iminium salts with active methylene reagents
  作者：Angelo Ranise、Francesco Lucchesini、Matteo Caviglia、Silvana Alfei、Andrea Spallarossa、Chiara Caneva

  DOI：10.1016/j.tet.2013.10.086

  日期：2013.12

  Knoevenagel-type indoles is described. The method is based on the in situ reaction of indole iminium salts (four of them are fully characterized) with acyclic symmetrical and unsymmetrical active methylene reagents in the presence of triethylamine. In general, the overall yields are moderate to good. Some of relevant reaction parameters and steric effects affecting stereoselectivity are discussed.

  描述了一种简单的一锅法，用于立体选择性合成Knoevenagel型吲哚。该方法基于在三乙胺存在下吲哚亚胺盐（已充分表征其中的四种）与无环对称和不对称活性亚甲基试剂的原位反应。总的来说，总产量是中等至良好。讨论了影响立体选择性的一些相关反应参数和空间效应。