ethyl-[3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]amine | 793672-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: ethyl-[3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]amine
• 英文别名: N-ethyl-3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propan-1-amine
• CAS: 793672-16-9
• 化学式: C₁₅H₂₄N₂O
• 分子量: 248.368
• InChiKey: HUGHQQHVZCGHLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-萘磺酰氯 、 ethyl-[3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]amine 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 N-ethyl-N-[3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]naphthalene-1-sulfonamide
  参考文献：
  名称：

  Novel 5-HT₇ Receptor Inverse Agonists. Synthesis and Molecular Modeling of Arylpiperazine- and 1,2,3,4-Tetrahydroisoquinoline-Based Arylsulfonamides

  摘要：

  A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R-2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the a carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.

  DOI：

  10.1021/jm049743b
• 作为产物：
  描述：

  3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propionitrile 在 lithium aluminium tetrahydride 、 三氯化铝 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ethyl-[3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]amine
  参考文献：
  名称：

  Novel 5-HT₇ Receptor Inverse Agonists. Synthesis and Molecular Modeling of Arylpiperazine- and 1,2,3,4-Tetrahydroisoquinoline-Based Arylsulfonamides

  摘要：

  A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R-2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the a carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.

  DOI：

  10.1021/jm049743b

文献信息

• Novel 5-HT₇ Receptor Inverse Agonists. Synthesis and Molecular Modeling of Arylpiperazine- and 1,2,3,4-Tetrahydroisoquinoline-Based Arylsulfonamides
  作者：Erik S. Vermeulen、Marjan van Smeden、Anne W. Schmidt、Jeffrey S. Sprouse、Håkan V. Wikström、Cor J. Grol

  DOI：10.1021/jm049743b

  日期：2004.10.1

  A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R-2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the a carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.