N-(2-(1H-indol-3-yl)ethyl)propan-1-amine | 14121-09-6

• 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
• 英文名称: N-(2-(1H-indol-3-yl)ethyl)propan-1-amine
• 英文别名: (2-indol-3-yl-ethyl)-propyl-amine；(2-Indol-3-yl-aethyl)-propyl-amin；N-[2-(1H-indol-3-yl)ethyl]propan-1-amine
• CAS: 14121-09-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: KBFBIAGUZWNRFI-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  361.3±17.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-苯基-2-糠醛 、 N-(2-(1H-indol-3-yl)ethyl)propan-1-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到[2-(1H-indol-3-yl)ethyl][(5-phenylfuran-2-yl)methyl]propylamine
  参考文献：
  名称：

  Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties

  摘要：

  A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl) amino]methyl}furan-2-yl)phenol (1, 5-HT6R K-i = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R K-j= 25, 5-HT2AR K-i = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with procognitive properties. (C) 2019 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111857
• 作为产物：
  描述：

  2-(1H-indol-3-yl)-2-oxo-N-propylacetamide 在 四氢呋喃 、 lithium aluminium tetrahydride 作用下， 生成 N-(2-(1H-indol-3-yl)ethyl)propan-1-amine
  参考文献：
  名称：

  Barlow; Khan, British Journal of Pharmacology and Chemotherapy, 1959, vol. 14, p. 99,101

  摘要：

  DOI：

文献信息

• 一种钯催化合成四氢β-咔啉-1-酮类化合物的方法
  申请人：中国科学院兰州化学物理研究所苏州研究院

  公开号：CN107098900A

  公开（公告）日：2017-08-29

  本发明公开一种钯催化合成四氢β‑咔啉‑1‑酮类化合物的方法，使用一氧化碳作为羰基源，在常压下与色胺类化合物发生反应高效制备四氢β‑咔啉‑1‑酮类化合物。本发明的优点是使用了常压的一氧化碳气体作为羰基源，二价金属钯作为催化剂，高效地制备了具有很大应用前景的四氢β‑咔啉‑1‑酮类化合物。从生产和经济的角度讲，和高压反应相比，常压的一氧化碳气体很大程度上降低了反应的成本，提高了反应的可操作性。
• NOVEL COMPOSITIONS AND METHODS FOR TREATING CANCER
  申请人：Board of Regents, The University of Texas System

  公开号：US20130129812A1

  公开（公告）日：2013-05-23

  Provided herein are methods and compositions inter alia for treating diseases, including hyperproliferative diseases, migraine headaches, and depression.

  本文提供了用于治疗疾病的方法和组合物，包括治疗增生性疾病、偏头痛和抑郁症的方法和组合物。
• Novel Compositions and Methods for Treating Cancer
  申请人：Board of Regents, The University of Texas System

  公开号：US20150306077A1

  公开（公告）日：2015-10-29

  Provided herein are methods and compositions inter alia for treating diseases, including hyperproliferative diseases, migraine headaches, and depression.

  本文提供了治疗疾病的方法和组合物，包括治疗高增殖性疾病、偏头痛和抑郁症等疾病的方法和组合物。
• [EN] COMPLEXING AGENT SALT FORMULATIONS OF PHARMACEUTICAL COMPOUNDS<br/>[FR] FORMULATIONS SALINES DE COMPOSÉS PHARMACEUTIQUES À BASE D'AGENTS COMPLEXANTS
  申请人：BEXSON BIOMEDICAL INC

  公开号：WO2022109050A1

  公开（公告）日：2022-05-27

  Provided herein are pharmaceutical formulations and pharmaceutical compound salts which utilize complexing agents as counterions. Such formulations and salts are useful for treating a variety of disease and disorders.

  本文提供了药物制剂和药物化合物盐，其使用络合剂作为反离子。这些制剂和盐对治疗各种疾病和障碍有用。
• Pd/Cu Cocatalyzed Oxidative Tandem C–H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones
  作者：Hui Han、Shang-Dong Yang、Ji-Bao Xia

  DOI：10.1021/acs.joc.8b03266

  日期：2019.3.15

  The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.