1-benzylindoline-6-carboxylic acid (2,2-dimethoxyethyl)amide | 338959-31-2

• 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
• 英文名称: 1-benzylindoline-6-carboxylic acid (2,2-dimethoxyethyl)amide
• 英文别名: 1-Benzylindoline-6-carboxylic acid (2,2-dimethoxyethyl)amide；1-benzyl-N-(2,2-dimethoxyethyl)-2,3-dihydroindole-6-carboxamide
• CAS: 338959-31-2
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: KZIHNCDTXTWZLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzylindoline-6-carboxylic acid (2,2-dimethoxyethyl)amide 在 吡啶 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 生成 1-benzyl-2,3-dihydro-8-trifluoromethanesulfonyloxy-pyrrolo[3,2-g]isoquinoline
  参考文献：
  名称：

  8-Piperazinyl-2,3-dihydropyrrolo[3,2-g]isoquinolines: Potent, selective, orally bioavailable 5-HT1 receptor ligands

  摘要：

  The novel 8-piperazinyl-2,3-dihydropyrroloisoquinoline template was synthesized in nine steps. The template was N-substituted to give a series of compounds showing binding to human cloned 5-HT1A, 5-HT1B and 5-HT1D receptors with pK(i)'s greater than 9 and selectivities up to 1000-fold against other serotonin, dopamine and adrenergic receptors. Several compounds were shown to possess weak partial agonist activity in cloned receptors, which translated to antagonism in in vitro studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.042
• 作为产物：
  描述：

  1-benzylindoline-6-carboxylic acid 、 氨基乙醛缩二甲醇 在 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 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 16.0h， 以99%的产率得到1-benzylindoline-6-carboxylic acid (2,2-dimethoxyethyl)amide
  参考文献：
  名称：

  ISOQUINOLINE AND QUINAZOLINE DEIVATIVES HAVING A COMBINED 5HT1A, 5HT1B AND 5HT1D RECEPTOR ACTIVITY

  摘要：

  公开号：

  EP1228043B1

文献信息

• Isoquinoline and quinazoline derivatives having a combined 5HT1A, 5HT1B, and 5HT1D receptor activity
  申请人：Gaster Mary Laramie

  公开号：US20050239797A1

  公开（公告）日：2005-10-27

  The invention relates to novel isoquinoline and quinazoline derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders.

  本发明涉及具有药理活性的新异喹啉和喹唑啉衍生物，其制备方法，含有它们的组合物以及它们在治疗各种疾病中的应用。
• 8-Piperazinyl-2,3-dihydropyrrolo[3,2-g]isoquinolines: Potent, selective, orally bioavailable 5-HT1 receptor ligands
  作者：Tom D. Heightman、Laramie M. Gaster、Sarah L. Pardoe、Jean-Pierre Pilleux、Michael S. Hadley、Derek N. Middlemiss、Gary W. Price、Claire Roberts、Claire M. Scott、Jeannette M. Watson、Laurie J. Gordon、Vicky A. Holland、Jenifer Powles、Graham J. Riley、Tania O. Stean、Brenda K. Trail、Neil Upton、Nigel E. Austin、Andrew D. Ayrton、Tanya Coleman、Leanne Cutler

  DOI：10.1016/j.bmcl.2005.06.042

  日期：2005.10

  The novel 8-piperazinyl-2,3-dihydropyrroloisoquinoline template was synthesized in nine steps. The template was N-substituted to give a series of compounds showing binding to human cloned 5-HT1A, 5-HT1B and 5-HT1D receptors with pK(i)'s greater than 9 and selectivities up to 1000-fold against other serotonin, dopamine and adrenergic receptors. Several compounds were shown to possess weak partial agonist activity in cloned receptors, which translated to antagonism in in vitro studies. (c) 2005 Elsevier Ltd. All rights reserved.
• ISOQUINOLINE AND QUINAZOLINE DEIVATIVES HAVING A COMBINED 5HT1A, 5HT1B AND 5HT1D RECEPTOR ACTIVITY
  申请人：SmithKline Beecham plc

  公开号：EP1228043B1

  公开（公告）日：2005-01-12