2-thienylmethylene tryptamine | 6716-71-8

• 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-thienylmethylene tryptamine
• 英文别名: N-(2-thienylidene)-triptamine；2-(1H-indol-3-yl)-N-(2-thienylmethylene)ethanamine；N-[2-(1H-indol-3-yl)ethyl]-1-thiophen-2-ylmethanimine
• CAS: 6716-71-8
• 化学式: C₁₅H₁₄N₂S
• 分子量: 254.356
• InChiKey: CQWLPYFIKBUJDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-thienylmethylene tryptamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以100%的产率得到2-(1H-indol-3-yl)-N-(thiophen-2-ylmethyl)ethan-1-amine
  参考文献：
  名称：

  合成新型不对称取代仲胺的可扩展方法

  摘要：

  探索了快速，简便，可扩展的方法，用于通过还原胺化合成包含萘，吲哚，吡啶和咪唑部分的不对称取代的仲胺。所研究的操作程序在50至30 mmol的规模上是成功的，并且具有扩大规模的巨大潜力。

  DOI：

  10.2298/jsc110408173r
• 作为产物：
  描述：

  2-噻吩甲醛 、 色胺 以 苯 为溶剂， 反应 4.0h， 以70%的产率得到2-thienylmethylene tryptamine
  参考文献：
  名称：

  合成新型不对称取代仲胺的可扩展方法

  摘要：

  探索了快速，简便，可扩展的方法，用于通过还原胺化合成包含萘，吲哚，吡啶和咪唑部分的不对称取代的仲胺。所研究的操作程序在50至30 mmol的规模上是成功的，并且具有扩大规模的巨大潜力。

  DOI：

  10.2298/jsc110408173r

文献信息

• Synthesis, Testing and Structure-Activity Studies on a Library of 5-HT4 Ligands
  作者：Amir Hanna-Elias、David T. Manallack、Alla Levit、William Nguyen、Fadi Ayad、Glen Perera、Marina Shapiro、Helen R. Irving、Ian M. Coupar、Magdy N. Iskander

  DOI：10.2174/157340610793563965

  日期：2010.11.1

  Several indole derivatives and analogues comprising a range of related structural classes were designed, synthesized and tested as ligands for the 5-HT4 receptor. Within each series, binding experiments showed compounds with good affinity demonstrating high percentage displacement values at 1 µM. The most potent of these (20) had a pKi of 8.54 demonstrating very good affinity. These indole analogues were combined with 55 ligands that were previously produced in our laboratory to explore the structure-activity relationships of these 5-HT4 ligands. A CoMFA (Comparative Molecular Field Analysis) analysis was used to extend an earlier simple pharmacophore to suggest two new molecular features beyond the primary amino binding site. The pharmacophore confirmed that a newly described tetrahydroquinoline analogue was able to match the basic requirements of the model and the pharmacology of this molecule is provided in more detail.

  设计、合成并测试了几种吲哚衍生物及其类似物，这些化合物属于一系列相关的结构类别，作为 5-HT4 受体的配体。在每个系列中，结合实验显示具有良好亲和力的化合物在 1 µM 浓度下表现出高百分比的置换值。其中最有效的化合物（20）的 pKi 值为 8.54，显示出非常好的亲和力。这些吲哚类似物与之前在我们实验室合成的 55 种配体相结合，以探索这些 5-HT4 配体的结构-活性关系。通过比较分子场分析（CoMFA），从早期简单的药效团模型延伸出两个新的分子特征，超越了主要的氨基结合位点。该药效团确认了一种新描述的四氢喹啉类似物能够匹配模型的基本要求，并且该分子的药理学特性有更详细的说明。
• Copper‐Catalyzed Chemoselective Divergent Carbene Insertion into the N−H bonds of Tryptamines
  作者：Dharmendra Kumar、Malleswara Rao Kuram

  DOI：10.1002/adsc.202300893

  日期：2023.11.21

  synthesis. Herein, we have developed a chemoselective copper-catalyzed carbene insertion protocol onto N−H bonds of tryptamine derivatives. Divergent insertion products are obtained by varying the nucleophilicity of the aliphatic NH of tryptamine with electron-donating or electron-withdrawing groups. The reaction provided N−H insertion products with broad substrate scope in good yields.

  轻松获得具有化学选择性的不同产物在有机合成中非常重要。在此，我们开发了一种化学选择性铜催化卡宾插入色胺衍生物 N−H 键的方案。通过改变色胺的脂肪族NH与给电子或吸电子基团的亲核性来获得不同的插入产物。该反应以良好的产率提供了具有广泛底物范围的 NH 插入产物。
• Ru(II)-Catalyzed β-Carboline Directed C–H Arylation and Isolation of Its Cycloruthenated Intermediates
  作者：Subramani Rajkumar、Shanmugam Karthik、Thirumanavelan Gandhi

  DOI：10.1021/acs.joc.5b00411

  日期：2015.6.5

  A Ru(II)-catalyzed C-H arylation approach has been developed utilizing beta-carboline alkaloids as the directing group. Selective formations of diarylated products from moderate to excellent yields were accomplished. Broad substrate scope with excellent functional group tolerance for C1-phenyl/thienyl/PAHs-beta-carbolines was demonstrated. X-ray crystal structure of cycloruthenated complex 2cr and no arylation reaction with model substrate 13 strongly suggests that N2 is the directing group than N9 in C1-aryl-beta-carbolines. Catalytic properties and stability of the cycloruthenated complexes have been explored. Library of biologically relevant new,beta-carboline derivatives and isolation of its cycloruthenated intermediates are the highlights of this work
• Foye, William O.; Wang, Xiping; Hongfu, Wang, Medicinal Chemistry Research, 1997, vol. 7, # 3, p. 180 - 191
  作者：Foye, William O.、Wang, Xiping、Hongfu, Wang

  DOI：——

  日期：——
• 1,3-Dipolar cycloaddition of 3,4-dihydro-6,7-dimethoxyisoquinoline- N -methoxycarbonyl methylide with Schiff bases
  作者：Áron Szöllősy、Thomas Tischer、István Kádas、László Tőke、Gábor Tóth

  DOI：10.1016/s0040-4020(99)00354-3

  日期：1999.6