3-(2-氨基乙基)-6-甲氧基吲哚 | 2736-21-2

• 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
• 中文名称: 3-(2-氨基乙基)-6-甲氧基吲哚
• 中文别名: [2-(6-甲氧基-1H-吲哚-3-基)-乙基]胺盐酸盐
• 英文名称: 6-methoxytryptamine hydrochloride
• 英文别名: 2-(6-methoxy-1H-indol-3-yl)ethanamine;hydrochloride
• CAS: 2736-21-2
• 化学式: C₁₁H₁₄N₂O*ClH
• 分子量: 226.706
• InChiKey: ANTAOYZCCFNXOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.04
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(2-氨基乙基)-6-甲氧基吲哚 在 水 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-methoxy-2-(4-phenylbutyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole
  参考文献：
  名称：

  Structure-activity relationship for a series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles: Potent subtype-selective inhibitors of (NMDA) receptors

  摘要：

  series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b] indoles was synthesized as potential antagonists for the NR1A/2B subtype of N-methyl-D-aspartate (NMDA) receptors. Assayed by electrical recording under steady-state conditions, 7-hydroxy-2-(4-phenylbutyl)-1,2,3,4-tetrahydropyrido-[3,4-b]indole (30) was the most potent compound in the series having an IC50 value of 50 nM at the MR1A/2B receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00248-6

文献信息

• Total Synthesis of an Anticancer Natural Product (±)-Peharmaline A and Its Analogues
  作者：Akshay S. Kulkarni、Rahul D. Shingare、Rambabu Dandela、D. Srinivasa Reddy

  DOI：10.1002/ejoc.201800949

  日期：2018.12.13

  The first total synthesis of the anticancer natural product (±)‐peharmaline A was accomplished in three steps. A stereoselective Pictet–Spengler reaction followed by the construction of the vasicinone moiety in a one‐pot fashion are the highlights. The developed route is useful to access peharmaline analogues, which opens opportunities for systematic structure–activity relationship studies during biological

  抗癌天然产物（±）-Peharmaline A的第一个全合成过程分三个步骤完成。亮点是立体选择性Pictet-Spengler反应，然后以一锅法构建vasicinone部分。发达的途径可用于获得peharmaline类似物，这为生物学评估期间进行系统的结构-活性关系研究提供了机会。
• Structure-activity relationships for substrates and inhibitors of pineal 5-hydroxytryptamine-N-acetyltransferase: preliminary studies
  作者：Shuren Shen、Béatrice Brémont、Isabelle Serraz、Jean Andrieux、Annie Poncet、Monique Mathé-Allainmat、Evelyne Chanut、Jean-Hugues Trouvin、Michel Langlois

  DOI：10.1016/0014-2999(96)00228-2

  日期：1996.6

  derivatives and no clear structure-activity relationship was observed. Melatonin and several bioisosteric derivatives were shown to be inhibitors of 5-HT-N-acetyltransferase. Preliminary data suggested that over the 5-50-microM concentration range, melatonin was a competitive inhibitor (IC50 = 10 microM) with a concentration-dependent inhibitory effect on its own synthesis in the pineal gland. However, the

  色胺，（1-萘基）乙胺和苯乙胺衍生物作为绵羊松果体5-羟色胺-N-乙酰基转移酶（5-HT-NAT）的底物进行了测试，后者是褪黑素合成的关键酶。几乎所有的吲哚衍生物都具有与色胺类似的亲和力（Km = 0.05 mM），而取代的萘和苯基衍生物的效价较低。但是，Km值似乎受取代基的位阻和极性性质影响。萘和苯基衍生物的Vmax值通常比吲哚衍生物的Vmax值高10-20倍，并且未观察到明确的结构活性关系。褪黑激素和几种生物等位衍生物被证明是5-HT-N-乙酰基转移酶的抑制剂。初步数据表明，在5-50 microM的浓度范围内，褪黑激素是一种竞争性抑制剂（IC50 = 10 microM），对松果体自身的合成具有浓度依赖性的抑制作用。然而，生物等位萘衍生物被表征为混合抑制剂。公认的褪黑素能拮抗剂（1-萘基）乙基乙酰氨基也被证明是5-HT-N-乙酰基转移酶的抑制剂（IC50 = 8 microM），是调
• Identification of new modulator of DNA repairing pathways based on natural product (±)-peharmaline A
  作者：Akshay S. Kulkarni、Anshurekha Dash、Rahul D. Shingare、Jagdish Chand、Diksha Manhas、Aman Singh、Utpal Nandi、Anindya Goswami、D. Srinivasa Reddy

  DOI：10.1016/j.bmc.2023.117365

  日期：2023.8

  (±)-peharmaline A, a hybrid natural product isolated from seeds of Peganum harmala L. possesses significant cytotoxic activities. Herein, we have described the design, and synthesis of a novel library of close and simplified analogues around the anticancer natural product (±)-peharmaline A and investigated their cytotoxic activities, which led to the identification of three structurally simplified lead compounds

  肿瘤块复杂的异质环境通常会导致耐药性并促进化疗不敏感，从而在癌症患者中引发更多的恶性表型。事实证明，主要的 DNA 损伤性癌症药物在提高化疗耐药性方面并不成功。(±)-peharmaline A 是从骆驼蓬种子中分离出来的杂种天然产物，具有显着的细胞毒活性。在此，我们描述了围绕抗癌天然产物 (±)-peharmaline A 的新型紧密和简化类似物库的设计和合成，并研究了它们的细胞毒性活性，从而鉴定了三种结构简化的先导化合物，它们表现出更好的效力比母体天然产物。其中，peharmaline A 的去甲氧基类似物的抗癌潜力被进一步研究，促使去甲氧基类似物作为有效的 DNA 损伤诱导剂，减弱负责 DNA 损伤修复的蛋白质的表达。因此，这种去甲氧基类似物需要进行详细的研究，以确认其抗癌活性的基于分子机制的研究。 __________________________________________
• Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus
  作者：James E. Audia、Deborah A. Evrard、Gwyn R. Murdoch、James J. Droste、Jeffrey S. Nissen、Kathy W. Schenck、Pawel Fludzinski、Virginia L. Lucaites、David L. Nelson、Marlene L. Cohen

  DOI：10.1021/jm960062t

  日期：1996.1.1

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.
• Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives
  作者：N. T. Pohodylo、V. S. Matiichuk、M. D. Obushak

  DOI：10.1134/s1070428014020225

  日期：2014.2

  Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-beta-carbolines that can be transformed into beta-carboline and tetrahydro-beta-carboline derivatives.