1-(Quinolin-5-carbonyl)-2,3-dihydro-8-(4-methylpiperazin-1-yl)pyrrolo[3,2-g]isoquinoline | 735256-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(Quinolin-5-carbonyl)-2,3-dihydro-8-(4-methylpiperazin-1-yl)pyrrolo[3,2-g]isoquinoline
• 英文别名: [2,3-Dihydro-8-(4-methyl-1-piperazinyl)-1H-pyrrolo[3,2-g]isoquinolin-1-yl]-5-quinolinylmethanone；[8-(4-methylpiperazin-1-yl)-2,3-dihydropyrrolo[3,2-g]isoquinolin-1-yl]-quinolin-5-ylmethanone
• CAS: 735256-31-2
• 化学式: C₂₆H₂₅N₅O
• 分子量: 423.517
• InChiKey: WBFASLOAEQLKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-benzyl-2,3-dihydro-8-trifluoromethanesulfonyloxy-pyrrolo[3,2-g]isoquinoline 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 达卡巴嗪 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(Quinolin-5-carbonyl)-2,3-dihydro-8-(4-methylpiperazin-1-yl)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

文献信息

• 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
• 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.