3-[2-(2,3-dihydro-1H-indol-1-yl)ethyl]-1H-indole | 129697-29-6

• 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: 3-[2-(2,3-dihydro-1H-indol-1-yl)ethyl]-1H-indole
• 英文别名: 3-[2-(2,3-dihydroindol-1-yl)ethyl]-1H-indole；3-(2-(1-indolinyl)ethyl)indole；1-(2-(1H-Indol-3-yl)ethyl)indoline
• CAS: 129697-29-6
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: JFNPAIFYPYOSES-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• 沸点：
  485.5±33.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-[2-(2,3-dihydro-1H-indol-1-yl)ethyl]-1H-indole 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 60.0h， 以55%的产率得到3-[2-(indol-1-yl)ethyl]-1H-indole
  参考文献：
  名称：

  Fascaplysin启发的二吲哚类化合物作为CDK4 / cyclin D1的选择性抑制剂

  摘要：

  我们目前的设计，合成和一个新的一系列取代的3-（2-（1的生物活性的ħ -吲哚-1-基）乙基）-1 ħ -indoles和1,2-二（1 ħ -吲哚-1-烷基）烷烃作为CDK4 /细胞周期蛋白D1的选择性抑制剂。设计这些化合物以探索吲哚基部分的连接模式与其CDK抑制活性之间的关系。与紧密相关的CDK2 / cyclin A相比，我们发现所有上述设计的化合物都是CDK4 / cyclin D1的选择性抑制剂，最佳化合物10m和13a的IC 50分别为39和37μm。

  DOI：

  10.1016/j.bmc.2009.06.070
• 作为产物：
  描述：

  吲哚 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.5h， 生成 3-[2-(2,3-dihydro-1H-indol-1-yl)ethyl]-1H-indole
  参考文献：
  名称：

  The design and synthesis of novel 3-[2-indol-1-yl-ethyl]-1H-indole derivatives as selective inhibitors of CDK4

  摘要：

  We present the design, synthesis and biological activity of novel 3-[2-indol-1-yl-ethyl]-1H-indole selective inhibitors of CDK4. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.054

文献信息

• Total synthesis of the marine sponge pigment fascaplysin
  作者：Benjamin Pelcman、Gordon W Gribble

  DOI：10.1016/s0040-4039(00)97367-2

  日期：——

  Fascaplysin (1), an antimicrobial and cytotoxic red pigment from the marine sponge Fascaplysinopsis sp., has been synthesized in seven steps from indole (65% yield). The pivotal intermediate in the synthesis is diindole 3 which is induced to undergo acid-catalyzed cyclization and dehydrogenation to afford the desired pentacycle 2 in > 90% yield. Peracid oxidation of 2 yields fascaplysin.

  Fascaplysin（1）是一种来自海洋海绵Fascaplysinopsis sp。的抗微生物和细胞毒性的红色颜料，已从吲哚经过7个步骤合成（产率为65％）。合成中的关键中间体是二吲哚3，该二吲哚3进行了酸催化的环化和脱氢反应，以90％以上的收率提供了所需的五环化合物2。2的过酸氧化会产生fascaplysin。
• Total syntheses of the marine sponge pigments fascaplysin and homofascaplysin B and C
  作者：Gordon W. Gribble、Benjamin Pelcman

  DOI：10.1021/jo00039a024

  日期：1992.6

  The Fascaplysinopsis spp. marine sponge pigments fascaplysin (1), homofascaplysin B (4), and homofascaplysin C (5) have been synthesized by peracid oxidation, reaction with oxalyl chloride/methanol, or Vilsmeier formylation, respectively, of the keystone intermediate 12H-pyrido[1,2-a:3,4-b']diindole (7). The versatile 7 was prepared from indole (17) in six steps (78% yield), a sequence in which the key reaction is the trifluoroacetic acid-induced ring closure of diindole 15, followed by Pd/C-catalyzed dehydrogenation of the crude mixture of cyclized products 25, 26, to give 7 in 93% yield from 15.
• Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives
  作者：Michael Decker、Thi Thanh Huyen Nguyen、Jochen Lehmann

  DOI：10.1016/j.tet.2004.03.073

  日期：2004.5

  The mechanism of lactamization of corresponding lactones was investigated by means of gas chromatography and synthesis of possible intermediates as references. Lactones react with amines via the amino acid with subsequent elimination of water to the corresponding lactams. In the first step, also hydroxyamides are in equilibrium with the lactones and amines, respectively, which are not able to form the amide though. This mechanism opens a new approach for the synthesis of N-beta-disubstituted tryptamines. (C) 2004 Elsevier Ltd. All rights reserved.
• PELCMAN, BENJAMIN;GRIBBLE, GORDON W., TETRAHEDRON LETT., 31,(1990) N7, C. 2381-2384
  作者：PELCMAN, BENJAMIN、GRIBBLE, GORDON W.

  DOI：——

  日期：——
• The design and synthesis of novel 3-[2-indol-1-yl-ethyl]-1H-indole derivatives as selective inhibitors of CDK4
  作者：Carine Aubry、Asma Patel、Sachin Mahale、Bhabatosh Chaudhuri、Jean-Didier Maréchal、Michael J. Sutcliffe、Paul R. Jenkins

  DOI：10.1016/j.tetlet.2005.01.054

  日期：2005.2

  We present the design, synthesis and biological activity of novel 3-[2-indol-1-yl-ethyl]-1H-indole selective inhibitors of CDK4. (C) 2005 Elsevier Ltd. All rights reserved.