1,3-diphenyl-2-[(2-phenyl-1H-indol-3-yl)methylene]propane-1,3-dione | 1355345-52-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-diphenyl-2-[(2-phenyl-1H-indol-3-yl)methylene]propane-1,3-dione
• 英文别名: 1,3-diphenyl-2-[(2-phenyl-1H-indol-3-yl)methylidene]propane-1,3-dione
• CAS: 1355345-52-6
• 化学式: C₃₀H₂₁NO₂
• 分子量: 427.502
• InChiKey: ZONIIHRGZBJQKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯基吲哚 在 溴化三(三苯基磷)铜 、 ammonium acetate 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 硝基甲烷 为溶剂， 反应 20.0h， 生成 1,3-diphenyl-2-[(2-phenyl-1H-indol-3-yl)methylene]propane-1,3-dione
  参考文献：
  名称：

  A novel NH4OAc and CuBr(PPh3)3-induced intermolecular Pummerer-type reaction between free (NH)-indoles and dimethylsulfoxide: facile synthesis of 3-methylthiomethyl substituted indoles

  摘要：

  A novel NH4OAc/CuBr(PPh3)(3)-induced intermolecular Pummerer-type reaction between free (NH)-indoles and dimethylsulfoxide is first reported, which offers the 3-methylthiomethyl substituted indoles conveniently and efficiently. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.002

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.