3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propionitrile | 793672-12-5

• 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: 3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propionitrile
• 英文别名: 3-(6-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)propanenitrile；3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propanenitrile
• CAS: 793672-12-5
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: IGEWIKFVSGGVEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 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：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 N-[3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propyl]acetamide
  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-1,2,3,4-四氢异喹啉盐酸盐 、 丙烯腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以96%的产率得到3-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)propionitrile
  参考文献：
  名称：

  TLR inhibitors

  摘要：

  通式（I）的化合物：其中变量的含义在说明书中解释，或其立体异构形式或立体异构形式的混合物，或其药学上可接受的盐。药物组合物可以包括本发明的化合物，可用于抑制TLR7/8受体的方法。

  公开号：

  US10689360B1

文献信息

• TLR 9 inhibitors
  申请人：Insilico Medicine IP Limited

  公开号：US11008303B2

  公开（公告）日：2021-05-18

  A method for inhibiting TLR9 includes contacting the TLR9 with compound of general formula (I): wherein the meanings of the variables are explained in the specification, or a stereoisomeric form or a mixture of stereoisomeric forms, or pharmaceutically acceptable salts thereof. A pharmaceutical composition can include compounds of the invention, which can be used in a method for inhibiting TLR9 activity in vitro or in vivo. The method can be performed by administering the compound to a subject to inhibit TLR9 activity, which can be used to treat a disease or disorder associated with TLR9.

  抑制 TLR9 的方法包括将 TLR9 与通式（I）的化合物接触：其中变量的含义在说明书中解释，或立体异构体形式或立体异构体形式的混合物，或其药学上可接受的盐。 药物组合物可包括本发明的化合物，其可用于体外或体内抑制 TLR9 活性的方法中。 该方法可以通过向受试者施用化合物来抑制 TLR9 活性，从而用于治疗与 TLR9 相关的疾病或紊乱。
• TLR INHIBITORS
  申请人：Insilico Medicine IP Limited

  公开号：EP3917920A1

  公开（公告）日：2021-12-08
• TLR 9 INHIBITORS
  申请人：Insilico Medicine IP Limited

  公开号：US20200290994A1

  公开（公告）日：2020-09-17

  A method for inhibiting TLR9 includes contacting the TLR9 with compound of general formula (I): wherein the meanings of the variables are explained in the specification, or a stereoisomeric form or a mixture of stereoisomeric forms, or pharmaceutically acceptable salts thereof. A pharmaceutical composition can include compounds of the invention, which can be used in a method for inhibiting TLR9 activity in vitro or in vivo. The method can be performed by administering the compound to a subject to inhibit TLR9 activity, which can be used to treat a disease or disorder associated with TLR9.
• [EN] TLR INHIBITORS<br/>[FR] INHIBITEURS DE TLR
  申请人：INSILICO MEDICINE IP LTD

  公开号：WO2020157620A1

  公开（公告）日：2020-08-06

  A compound of general formula (I), as shown herein, wherein the meanings of the variables are explained in the specification, or a stereoisomeric form or a mixture of stereoisomeric, or pharmaceutically acceptable salts thereof. A pharmaceutical composition can include the said compounds, which can be used in a method for inhibiting TLR7/8 receptors.
• 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.