2-(二甲基氨基)-1-(6-甲氧基吲哚啉-1-基)乙酮 | 793672-18-1

• 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
• 中文名称: 2-(二甲基氨基)-1-(6-甲氧基吲哚啉-1-基)乙酮
• 英文名称: 2-dimethylamino-1-(6-methoxy-2,3-dihydroindol-1-yl)ethanone
• 英文别名: 2-(Dimethylamino)-1-(6-methoxyindolin-1-yl)ethanone；2-(dimethylamino)-1-(6-methoxy-2,3-dihydroindol-1-yl)ethanone
• CAS: 793672-18-1
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: QVXLHCTWPKUDEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(二甲基氨基)-1-(6-甲氧基吲哚啉-1-基)乙酮 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以43%的产率得到[2-(6-methoxy-2,3-dihydroindol-1-yl)ethyl]dimethylamine
  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：

  6-甲氧基二氢吲哚 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 2-(二甲基氨基)-1-(6-甲氧基吲哚啉-1-基)乙酮
  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.