2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethanamine | 200629-88-5

• 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-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethanamine
• CAS: 200629-88-5
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: ZPPPHLDXNPNKKW-UHFFFAOYSA-N

物化性质

• 沸点：
  497.602±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.170±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对联苯磺酰氯 、 2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethanamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-{2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethyl}-4-phenylbenzene-1-sulfonamide
  参考文献：
  名称：

  Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase

  摘要：

  A series of inhibitors of mammalian 15-lipoxygenase based on tryptamine and homotryptamine scaffolds is described. Compounds with aryl substituents at C-2 of the indole core of tryptamine and homotryptamine sulfonamides (e.g., 37a-p) proved to be potent inhibitors of the isolated enzyme. Selected compounds also demonstrated desirable inhibition selectivities over isozymes 5- and P-12-LO. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.081
• 作为产物：
  描述：

  2-bromo-N-phthaloyltryptamine 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 、 肼 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 生成 2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethanamine
  参考文献：
  名称：

  Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase

  摘要：

  A series of inhibitors of mammalian 15-lipoxygenase based on tryptamine and homotryptamine scaffolds is described. Compounds with aryl substituents at C-2 of the indole core of tryptamine and homotryptamine sulfonamides (e.g., 37a-p) proved to be potent inhibitors of the isolated enzyme. Selected compounds also demonstrated desirable inhibition selectivities over isozymes 5- and P-12-LO. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.081

文献信息

• Somatostatin antagonists and agonists
  申请人：——

  公开号：US20020091090A1

  公开（公告）日：2002-07-11

  Compounds according to the formula A-B-Z-W, wherein A is selected from (C 6 -C 10 )aryl-, or (C 1 -C 9 )heteroaryl-, which groups may be optionally substituted; B is selected from (a) O, NH, NR 10 , —(CH 2 ) k —O—, —(CH 2 ) k —N—, and —(CH 2 ) k —NR 10 —, where R 10 is (C 1 -C 6 )alkyl and where k is 1 to 6 in each case, or 1 where said group (i) through (iv) is optionally substituted by 1 to 4, preferably 1 to 2, groups selected from (C 1 -C 6 )alkyl, halo, and (C 1 -C 6 )alkyl optionally substituted by 1 to 3 halo atoms wherein one of carbon atoms C 1 , C 2 , C 3 and C 4 of said piperidine or piperazine group is optionally replaced by a carbonyl group; Z and W are as herein described; and pharmaceutically acceptable salts, solvates or hydrates thereof; pharmaceutical compositions thereof; and methods useful to facilitate secretion of growth hormone(GH) in mammels.

  根据公式A-B-Z-W，其中 A选自(C6-C10)芳基或(C1-C9)杂环芳基，这些基团可以选择性地被取代； B选自 (a) O、NH、NR10、—(CH2)k—O—、—(CH2)k—N—和—(CH2)k—NR10—，其中R10为(C1-C6)烷基，k在每种情况下为1至6，或 1所述的该组(i)至(iv)可以选择性地被1至4个，优选1至2个，选自(C1-C6)烷基、卤素和(C1-C6)烷基，该烷基可以选择性地被1至3个卤原子取代，其中所述哌啶或哌嗪基团的碳原子C1、C2、C3和C4中的一个可以选择性地被羰基取代； Z和W如本文所述；以及其药学上可接受的盐、溶剂化合物或水合物；其制药组合物；以及用于促进哺乳动物分泌生长激素(GH)的方法。
• Indole inhibitors of 15-lipoxygenase
  申请人：Weinstein S. David

  公开号：US20060063822A1

  公开（公告）日：2006-03-23

  The present invention provides indole inhibitors of 15-LO, pharmaceutical compositions containing such inhibitors and methods for treating diseases related to the 15-LO cascade using such compounds and compositions.

  本发明提供了15-LO的吲哚抑制剂，包含这些抑制剂的药物组合物以及使用这些化合物和组合物治疗与15-LO级联相关疾病的方法。
• Pd(II)-Catalyzed Intramolecular C(sp²)–H Arylation of Tryptamines Using the Nonsteric NH₂ as a Directing Group
  作者：Sixi Wang、Bin Yu、Hong-Min Liu

  DOI：10.1021/acs.orglett.0c03668

  日期：2021.1.1

  The free amine-directed C–H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)–H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope

  游离胺指导的CH官能化反应具有挑战性，主要限于笨重的胺。在这项工作中，我们报告了非立体NH 2定向的Pd（II）催化的类固醇胺的分子内C（sp 2）–H芳基化反应，从而可以高效，克级和区域选择性地合成通用的2-芳基色胺（35个例子，最高可达98％）。这种方法拓宽了游离胺导向的C–H官能化的底物范围，而不仅限于笨重的胺底物。2-芳基色胺的后期精加工实现了复杂核心结构的多样化构建，这种结构在极有价值的天然产物（如金盏花石，鸟嘌呤和草碱）中普遍存在。
• 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。
• US7429611B2
  申请人：——

  公开号：US7429611B2

  公开（公告）日：2008-09-30