3-[3-(二甲基氨基)丙基]-1H-吲哚 | 13117-35-6

• 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
• 中文名称: 3-[3-(二甲基氨基)丙基]-1H-吲哚
• 中文别名: 3-(1H-吲哚-3-基)-N,N-二甲基丙烷-1-胺
• 英文名称: N-Dimethylhomotryptamine
• 英文别名: 3-(1H-indol-3-yl)-N,N-dimethylpropan-1-amine；(3-indol-3-yl-propyl)-dimethyl-amine；3-(γ-Dimethylaminopropyl)-indol；3-(3-Dimethylpropylamino)indol；N-Dimethylhomotryptamin
• CAS: 13117-35-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: QHNWPRMHGXRBAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-[3-(二甲基氨基)丙基]-1H-吲哚 在 三氯氧磷 作用下， 反应 6.0h， 生成 3-[1-[3-(3-Dimethylamino-propyl)-1H-indol-2-yl]-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide
  参考文献：
  名称：

  Design and synthesis of aminopropyl tetrahydroindole-based indolin-2-ones as selective and potent inhibitors of Src and Yes tyrosine kinase

  摘要：

  A novel series of substituted 3-[3-(aminopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydro-indole-2-ones was discovered as potent inhibitors of the non-receptor tyrosine kinase Src and Yes. A structure-activity relationship was developed in order to optimize their potency and selectivity. Syntheses of these compounds are also described herein. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.069
• 作为产物：
  描述：

  3-吲哚丙酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[3-(二甲基氨基)丙基]-1H-吲哚
  参考文献：
  名称：

  Design and synthesis of aminopropyl tetrahydroindole-based indolin-2-ones as selective and potent inhibitors of Src and Yes tyrosine kinase

  摘要：

  A novel series of substituted 3-[3-(aminopropyl)-4,5,6,7-tetrahydro-1H-indol-2-ylmethylene]-1,3-dihydro-indole-2-ones was discovered as potent inhibitors of the non-receptor tyrosine kinase Src and Yes. A structure-activity relationship was developed in order to optimize their potency and selectivity. Syntheses of these compounds are also described herein. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.069

文献信息

• 吲哚衍生物及其在药物上的应用
  申请人：广东东阳光药业有限公司

  公开号：CN104276993B

  公开（公告）日：2019-03-15

  本发明提供一些吲哚衍生物或其立体异构体，互变异构体，氮氧化物，溶剂化物，代谢产物，药学上可接受的盐或前药，用于治疗阿尔茨海默症。本发明还公开了含有这样的化合物的药物组合物和使用本发明化合物或其药物组合物治疗阿尔茨海默症的方法。
• Indole AHR inhibitors and uses thereof
  申请人：Kyn Therapeutics

  公开号：US10570138B2

  公开（公告）日：2020-02-25

  The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

  本发明提供了可用作 AHR 抑制剂的化合物、其组合物及其使用方法。
• Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)
  作者：William D. Schmitz、Derek J. Denhart、Allison B. Brenner、Jonathan L. Ditta、Ronald J. Mattson、Gail K. Mattson、Thaddeus F. Molski、John E. Macor

  DOI：10.1016/j.bmcl.2005.01.059

  日期：2005.3

  A series of N,N-dimethylhomotryptamines was prepared and their binding affinities at the serotonin transporter (SERT) were determined. Compounds possessing an electron withdrawing substituent at the C5-position of the indole nucleus were found to be potent SSRIs. Initial attempts at conformational restriction of the propylamine sidechain by incorporation of a quinuclidine bicyclic structure did not improve binding affinity at SERT. (c) 2005 Elsevier Ltd. All rights reserved.
• One-pot synthesis of homotryptamines from indoles
  作者：Derek J. Denhart、Ronald J. Mattson、Jonathan L. Ditta、John E. Macor

  DOI：10.1016/j.tetlet.2004.03.070

  日期：2004.5

  A method is presented for the one-pot synthesis of homotryptamines by the MacMillan reaction of indoles with acrolein followed by reductive amination. (C) 2004 Elsevier Ltd. All rights reserved.
• Binding of Serotonin to the Human Serotonin Transporter. Molecular Modeling and Experimental Validation
  作者：Leyla Celik、Steffen Sinning、Kasper Severinsen、Carsten G. Hansen、Maria S. Møller、Mikael Bols、Ove Wiborg、Birgit Schiøtt

  DOI：10.1021/ja076403h

  日期：2008.3.1

  Molecular modeling and structure-activity relationship studies were performed to propose a model for binding of the neurotransmitter serotonin (5-HT) to the human serotonin transporter (hSERT). Homology models were constructed using the crystal structure of a bacterial homologue, the leucine transporter from Aquifex aeolicus, as the template and three slightly different sequence alignments. Induced fit docking of 5-HT into hSERT homology models resulted in two different binding modes. Both show a salt bridge between Asp98 and the charged primary amine of 5-HT, and both have the 5-HT C6 position of the indole ring pointing toward Ala173. The difference between the two orientations of 5-HT is an enantiofacial discrimination of the indole ring, resulting in the 5-hydroxyl group of 5-HT being vicinal to either Ser438/ Thr439 or Ala169/lle172/Ala173. To assess the binding experimentally, binding affinities for 5-HT and 17 analogues toward wild type and 13 single point mutants of hSERT were measured using an approach termed paired mutant-ligand analogue complementation (PaMLAC). The proposed ligand-protein interaction was systematically examined by disrupting it through site-directed mutagenesis and reestablishing another interaction via a ligand analogue matching the mutated residue, thereby minimizing the risk of identifying indirect effects. The interactions between Asp98 and the primary amine of 5-HT and the interaction between the C6-position of 5-HT and hSERT position 173 was confirmed using PaMLAC. The measured binding affinities of various mutants and 5-HT analogues allowed for a distinction between the two proposed binding modes of 5-HT and biochemically support the model for 5-HT binding in hSERT where the 5-hydroxyl group is in close proximity to Thr439.