2-(5-ethyl-1H-indol-3-yl)ethylamine | 62500-88-3

• 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: 2-(5-ethyl-1H-indol-3-yl)ethylamine
• 英文别名: 5-ethyltryptamine；1H-Indole-3-ethanamine, 5-ethyl-；2-(5-ethyl-1H-indol-3-yl)ethanamine
• CAS: 62500-88-3
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: HNICQKBUQQHUMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(5-ethyl-1H-indol-3-yl)ethylamine 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 6-ethyl-1-(3-methoxyphenyl)-2-nonyl-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Antioxydant activity of β-carboline derivatives in the LDL oxidation model

  摘要：

  A series of beta-carboline compounds were synthesized, starting from compound GWC22, their antioxidant activity was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO4 or 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH). The protective actions of these compounds against the cytotoxicity were evaluated with lactate dehydrogenase (LDH) activity in bovine aortic endothelial cells (BAECs) and cellular vitality by measuring mitochondrial activity in the presence of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). Most of compounds showed an higher antioxidant activity than GWC22 derivative (R = 1.6 for 5 mu M CuSO4). The best antioxidant activities are phenolic and benzyloxy derivatives with ratio R = 1.9 to 2.8 for 1 mu M CuSO4. These substances have protective actions and increase significantly the cell viability. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.048
• 作为产物：
  描述：

  5-乙基吲哚 在 ammonium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 101.0h， 生成 2-(5-ethyl-1H-indol-3-yl)ethylamine
  参考文献：
  名称：

  血清素的O-烷基衍生物在人5-HT1Dβ受体上的结合。

  摘要：

  在人类中，5-HT1D血清素受体代表末端自身受体，并且有一些证据表明5-HT1D配体可用于治疗偏头痛。最广泛使用的5-HT1D激动剂是舒马普坦。然而，据报道该试剂对5-HT1D的选择性相对于5-HT1A受体几乎没有。为了鉴定具有增强的5-HT1D相对于5-HT1A选择性的新型5-羟色胺能药物，我们尝试利用与这两个受体的5-HT结合位点的5-位相关的体积耐受性区域中的可能差异。对一系列5-（烷氧基）色胺的衍生物的研究表明，具有多达8个碳原子的直链烷基的化合物以高亲和力与人5-HT1Dβ受体结合（Ki < 5 nM），但相对于5-HT1A受体，选择性不足50倍。长于八个碳原子的烷基会降低对5-HT1A受体的亲和力，而长于九个碳原子的烷基会导致对5-HT1Dβ受体的亲和力降低的化合物。5-（壬氧基）色胺（10）代表具有最佳5-HT1Dβ亲和力（Ki = 1 nM）和选择性（> 300倍）的化合物。烷基链分支成5-[（（7

  DOI：

  10.1021/jm950498t

文献信息

• <i>N</i>-Methyl-5-<i>tert</i>-butyltryptamine:  A Novel, Highly Potent 5-HT_1D Receptor Agonist
  作者：Yao-Chang Xu、John M. Schaus、Clint Walker、Joe Krushinski、Nika Adham、John M. Zgombick、Sidney X. Liang、Dan T. Kohlman、James E. Audia

  DOI：10.1021/jm9805945

  日期：1999.2.1

  one heteroatom (N, O, or S) on the 5-substituent of the indole. This has led to the hypothesis that a 5-substituent capable of participating in hydrogen bonding is critical for conveying high affinity. This article describes the synthesis and biological evaluation of a new series of 5-alkyltryptamine analogues, which does not have a heteroatom in the 5-substituent group. In contrast to the hypothesis

  已经观察到报道的5-HT1D受体激动剂在吲哚的5-取代基上具有至少一个杂原子（N，O或S）。这导致了这样的假设：能够参与氢键的5-取代基对于传达高亲和力至关重要。本文介绍了一系列新的5-烷基色胺类似物的合成和生物学评估，这些类似物在5-取代基中没有杂原子。与该假设相反，5-烷基色胺都对人5-HT1D受体表现出高结合亲和力。在吲哚的5-位的亲脂性烷基的大小对5-HT1D结合亲和力具有显着影响。鉴定了在5-位具有叔丁基的化合物，例如9d，10和11。这些类似物显示出高结合亲和力（Ki <
• A mild and efficient route to 2-benzyl tryptamine derivatives via ring-opening of β-carbolines
  作者：Fariza Hadjaz、Saïd Yous、Nicolas Lebegue、Pascal Berthelot、Pascal Carato

  DOI：10.1016/j.tet.2008.07.056

  日期：2008.10

  described a mild and easy method, in two steps, by which various benzyl groups were introduced in the C-2 position of tryptamine. The first step consisted on the synthesis of β-carbolines, starting from tryptamine derivatives, by a Pictet–Spengler reaction. Ring-opening of the β-carbolines, by hydrogenation, led to the desired 2-substituted benzyl tryptamine indole products. A supplementary step of alkylation

  我们分两步描述了一种温和而简便的方法，通过该方法，将多种苄基引入色胺的C-2位置。第一步包括通过Pictet-Spengler反应从色胺胺衍生物开始合成β-咔啉。通过氢化使β-咔啉开环，得到所需的2-取代的苄基色胺为吲哚产物。可以实现烷基化的补充步骤，以得到N-烷基-2-取代的苄基色胺。在这些反应过程中，氮原子不需要任何保护步骤。
• Vinylogous acid derivatives
  申请人：Banner David

  公开号：US20070129421A1

  公开（公告）日：2007-06-07

  The invention is concerned with vinylogous acids derivatives of formula (I) wherein A and R 1 to R 6 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit chymase and can be used as medicaments.

  本发明涉及式(I)的烯丙基酸衍生物，其中A和R1到R6如说明书和权利要求所定义，以及其生理上可接受的盐。这些化合物抑制chymase并可用作药物。
• Enantioselective intramolecular Pictet–Spengler type annulation of indole-linked 3-methyleneisoindolin-1-ones
  作者：Min Liu、Wenzhe Li、Min Huang、Yingkun Yan、Min Li、Lianyi Cao、Xiaomei Zhang

  DOI：10.1039/d2nj00517d

  日期：——

  An enantioselective intramolecular Pictet–Spengler type annulation of indole-linked 3-methyleneisoindolin-1-ones was developed by using a chiral phosphoric acid as a catalyst. This method enabled the construction of a series of chiral isoindolinone fused tetrahydro β-carbolines in moderate to good yields (up to 97%) with moderate to good enantioselectivities (up to 96% ee). Furthermore, an α1-AR antagonist

  通过使用手性磷酸作为催化剂，开发了吲哚连接的 3-亚甲基异吲哚啉-1-酮的对映选择性分子内 Pictet-Spengler 型环化。该方法能够以中等至良好的产率（高达 97%）和中等至良好的对映选择性（高达 96% ee）构建一系列手性异吲哚啉酮稠合四氢 β-咔啉。此外，通过还原一种产物制备α 1 -AR拮抗剂。因此，提供了一种方便的程序来构建具有生物活性的四氢 β-咔啉。
• Electrosynthesis of Spiro-indolenines via Dearomative Arylation of Indoles in Batch and Continuous Flow
  作者：Wei Zhao、Yi Lu、Yaqi Qiao、Xing Yin、Chengkou Liu、Zheng Fang、Jianliang Zhu、Kai Guo

  DOI：10.1021/acs.orglett.3c03149

  日期：2023.10.13

  An electrosynthesis of spiro-indolenines in batch and continuous flow was achieved through dearomative arylation of indoles with good functional group compatibility. User-friendly undivided cells were used under catalyst- and oxidant-free conditions. Moreover, the use of a flow electrolysis cell gave high daily productivity and excellent scale-up potential under less supporting electrolyte and higher

  通过具有良好官能团相容性的吲哚脱芳香芳基化，实现了间歇和连续流中螺环吲哚的电合成。用户友好的未分割电池在无催化剂和氧化剂的条件下使用。此外，使用流动电解池在较少的支持电解质和较高的底物浓度条件下提供了较高的日生产率和优异的放大潜力。