N,N-dimethyl-2-[6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)indol-1-yl]ethanamine | 281202-87-7

• 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,N-dimethyl-2-[6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)indol-1-yl]ethanamine
• CAS: 281202-87-7
• 化学式: C₁₈H₂₅N₃
• 分子量: 283.417
• InChiKey: DDFMBYITCXTTPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  11.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-[6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)indol-1-yl]ethanamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 1-(2-(N,N-Dimethylamino)ethyl)-6-(N-methyl-2,3-dihydro-4-piperidinyl)-1H-indole
  参考文献：
  名称：

  Design, synthesis and biological activity of novel dimethyl-{2-[6-substituted-indol-1-yl]-ethyl}-amine as potent, selective, and orally-Bioavailable 5-HT 1D agonists

  摘要：

  A novel series of highly potent human 5-HT1D agonists, dimethyl-{2-[6-substituted-indol-1-yl]-ethyl}-amine, was synthesized. Structure-activity relationship (SAR) investigation revealed 4-[1-(2-dimethylamino-ethyl)-1H-indol-6-yl]-tetrahydro-thiopyran-4-ol, 11b (ALX-2732), as a potent (K-i = 2.4 nM) agonist at the human 5-HT1D receptor with good selectivity over the other serotonin receptor subtypes. This compound demonstrated favorable in vitro metabolic stability in human and rat liver microsomes and was found to be orally bioavailable in rats (F-po = 51%) (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.025
• 作为产物：
  描述：

  6-溴吲哚 在 叔丁基锂 、 potassium hydride 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N,N-dimethyl-2-[6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)indol-1-yl]ethanamine
  参考文献：
  名称：

  Design, synthesis and biological activity of novel dimethyl-{2-[6-substituted-indol-1-yl]-ethyl}-amine as potent, selective, and orally-Bioavailable 5-HT 1D agonists

  摘要：

  A novel series of highly potent human 5-HT1D agonists, dimethyl-{2-[6-substituted-indol-1-yl]-ethyl}-amine, was synthesized. Structure-activity relationship (SAR) investigation revealed 4-[1-(2-dimethylamino-ethyl)-1H-indol-6-yl]-tetrahydro-thiopyran-4-ol, 11b (ALX-2732), as a potent (K-i = 2.4 nM) agonist at the human 5-HT1D receptor with good selectivity over the other serotonin receptor subtypes. This compound demonstrated favorable in vitro metabolic stability in human and rat liver microsomes and was found to be orally bioavailable in rats (F-po = 51%) (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.025

文献信息

• Design, synthesis and biological activity of novel dimethyl-{2-[6-substituted-indol-1-yl]-ethyl}-amine as potent, selective, and orally-Bioavailable 5-HT 1D agonists
  作者：Methvin Isaac、Malik Slassi、Tao Xin、Jalaj Arora、Anne O'Brien、Louise Edwards、Neil MacLean、Julie Wilson、Lidia Demschyshyn、Phillipe Labrie、Angela Naismith、Shawn Maddaford、Damon Papac、Shuree Harrison、Hua Wang、Stan Draper、Ashok Tehim

  DOI：10.1016/j.bmcl.2003.09.025

  日期：2003.12

  A novel series of highly potent human 5-HT1D agonists, dimethyl-2-[6-substituted-indol-1-yl]-ethyl}-amine, was synthesized. Structure-activity relationship (SAR) investigation revealed 4-[1-(2-dimethylamino-ethyl)-1H-indol-6-yl]-tetrahydro-thiopyran-4-ol, 11b (ALX-2732), as a potent (K-i = 2.4 nM) agonist at the human 5-HT1D receptor with good selectivity over the other serotonin receptor subtypes. This compound demonstrated favorable in vitro metabolic stability in human and rat liver microsomes and was found to be orally bioavailable in rats (F-po = 51%) (C) 2003 Elsevier Ltd. All rights reserved.