tert-butyl (3S)-3-(2-piperidin-1-ylethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate | 869002-57-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3S)-3-(2-piperidin-1-ylethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 869002-57-3
• 化学式: C₂₂H₃₃N₃O₃
• 分子量: 387.522
• InChiKey: SCGNWFGRIYYTIF-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-(2-piperidin-1-ylethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (10aS)-2-(2-piperidin-1-ylethyl)-3-sulfanylidene-10,10a-dihydro-5H-imidazo[1,5-b]isoquinolin-1-one
  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
• 作为产物：
  描述：

  (S)-(-)-1,2,3,4-四氢异喹啉-3-羧酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 tert-butyl (3S)-3-(2-piperidin-1-ylethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
  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.