(10aS)-10,10a-Dihydro-7-hydroxy-2-[2-(1-piperidinyl)ethyl]imidazo[1,5-b]isoquinoline-1,3(2H,5H)-dione | 869002-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (10aS)-10,10a-Dihydro-7-hydroxy-2-[2-(1-piperidinyl)ethyl]imidazo[1,5-b]isoquinoline-1,3(2H,5H)-dione
• 英文别名: (10aS)-7-hydroxy-2-(2-piperidin-1-ylethyl)-10,10a-dihydro-5H-imidazo[1,5-b]isoquinoline-1,3-dione
• CAS: 869002-66-4
• 化学式: C₁₈H₂₃N₃O₃
• 分子量: 329.399
• InChiKey: GSXRASCGXBFYRC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二碘-L-酪氨酸 在 palladium on activated charcoal N-乙基哌啶 、 盐酸 、 sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 183.0h， 生成 (10aS)-10,10a-Dihydro-7-hydroxy-2-[2-(1-piperidinyl)ethyl]imidazo[1,5-b]isoquinoline-1,3(2H,5H)-dione
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of Tic-hydantoin derivatives as selective σ1 ligands. Part 1

  摘要：

  Herein is described a new class of selective sigma(1), ligands consisting of tetrahydroisoquinoline-hydantoin (Tic-hydantoin) derivatives. Compound 3a has high affinity (IC50 = 16 nM) for the (71 receptor and is selective in a large panel of therapeutic targets. This first study presents structural changes around the Tic-hydantoin core, leading to a Tic-hydantoin analogue with a higher sigma(1) affinity (IC50 approximate to 1 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.040

文献信息

• Synthesis and pharmacological evaluation of Tic-hydantoin derivatives as selective σ1 ligands. Part 1
  作者：Julie Charton、Amaury Cazenave Gassiot、Sophie Girault-Mizzi、Marie-Ange Debreu-Fontaine、Patricia Melnyk、Christian Sergheraert

  DOI：10.1016/j.bmcl.2005.07.040

  日期：2005.11

  Herein is described a new class of selective sigma(1), ligands consisting of tetrahydroisoquinoline-hydantoin (Tic-hydantoin) derivatives. Compound 3a has high affinity (IC50 = 16 nM) for the (71 receptor and is selective in a large panel of therapeutic targets. This first study presents structural changes around the Tic-hydantoin core, leading to a Tic-hydantoin analogue with a higher sigma(1) affinity (IC50 approximate to 1 nM). (c) 2005 Elsevier Ltd. All rights reserved.