2-氯-1-(6-甲氧基吲哚啉-1-基)乙酮 | 793672-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-氯-1-(6-甲氧基吲哚啉-1-基)乙酮
• 英文名称: 2-chloro-1-(6-methoxy-2,3-dihydroindol-1-yl)ethanone
• 英文别名: 2-Chloro-1-(6-methoxyindolin-1-yl)ethanone
• CAS: 793672-17-0
• 化学式: C₁₁H₁₂ClNO₂
• 分子量: 225.675
• InChiKey: POUZLWAQXVLYGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氯-1-(6-甲氧基吲哚啉-1-基)乙酮 在 lithium aluminium tetrahydride 、 三氯化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 [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-甲氧基吲哚 在 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-氯-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

• INDOLINE DERIVATIVES AS SEROTONERGIC AGENTS USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  申请人：[en]MINDSET PHARMA INC.

  公开号：WO2024044847A1

  公开（公告）日：2024-03-07

  The present application relates to methods of activating serotonin receptors in a cell using indoline derivatives of general Formula (I) or a pharmaceutically acceptable salt, solvate and/or prodrug thereof, as well as to treating diseases, disorders or conditions by activation of a serotonin receptors in a cell. The diseases, disorders or conditions include, for example, psychosis, mental illnesses and CNS disorders. The present application also relates to novel indoline derivatives and to compositions and uses thereof. Wherein Q is selected from (Q1), (Q2), (Q3), (Q4) (Q5) and (Q6).
• 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.