5-amino-2,3-dihydro-2,2-dimethylbenzofuran | 31010-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-amino-2,3-dihydro-2,2-dimethylbenzofuran
• 英文别名: 2,2-dimethyl-2,3-dihydro-benzofuran-5-ylamine；2,2-dimethyl-2,3-dihydrobenzofuran-5-amine；2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-amine；2,2-dimethyl-3H-1-benzofuran-5-amine
• CAS: 31010-94-3
• 化学式: C₁₀H₁₃NO
• mdl: MFCD16708763
• 分子量: 163.219
• InChiKey: LWDIQKVNWBXIMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-amino-2,3-dihydro-2,2-dimethylbenzofuran 在 吡啶 、 盐酸 、 四氯化钛 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 (2,2-Dimethyl-2,3-dihydro-benzofuran-5-yl)-(2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-yl)-amine
  参考文献：
  名称：

  5-Aminocoumarans:  Dual Inhibitors of Lipid Peroxidation and Dopamine Release with Protective Effects against Central Nervous System Trauma and Ischemia

  摘要：

  A series of 2,3-dihydro-5-benzofuranamines (5-aminocoumarans) were developed for the treatment of traumatic and ischemic central. nervous system (CNS) injury. Compounds within this class were extremely effective inhibitors of lipid peroxidation in vitro and antagonized excitatory behavior coupled with peroxidative injury induced by spinal intrathecal injection of FeCl2 (mouse-FeCl2-it assay) in vivo. Selected compounds were tested for antagonistic activity on methamphetamine (MAP)-induced hypermotility resulting from dopamine release in the mouse brain. Among the compounds synthesized, compound 26n (2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)meth]-5-benzofuranamine) exhibited potent effects in these assays (inhibition of lipid peroxidation, IC50 = 0.07 mu M; mouse-FeCl2-it assay, ID50 = 10.4 mg/kg, po; MAP-induced hypermotility, 98% inhibition, 10 mg/kg, ip). The S-(+)-form of compound 26n dihydrochloride (TAK-218), which has 30 times more potent antagonistic activity on MAP-induced hypermotility than the R-(-)-form, improved more significantly the survival rate in the cerebral ischemia model (rat, 1-3 mg/kg, ip) during the period of 1-14 days after ischemia and decreased functional disorders in the traumatic brain injury model (rat, 0.1-1 mg/kg, ip) 3-14 days after injury. These results imply a role for dopamine in deterioration of CNS function after ischemic and traumatic injury. TAK-218 is a promising compound for the treatment of stroke and CNS trauma and is now under clinical investigation.

  DOI：

  10.1021/jm960411j
• 作为产物：
  描述：

  4-羟基苯甲酰胺 在 盐酸 、 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-amino-2,3-dihydro-2,2-dimethylbenzofuran
  参考文献：
  名称：

  5-Aminocoumarans:  Dual Inhibitors of Lipid Peroxidation and Dopamine Release with Protective Effects against Central Nervous System Trauma and Ischemia

  摘要：

  A series of 2,3-dihydro-5-benzofuranamines (5-aminocoumarans) were developed for the treatment of traumatic and ischemic central. nervous system (CNS) injury. Compounds within this class were extremely effective inhibitors of lipid peroxidation in vitro and antagonized excitatory behavior coupled with peroxidative injury induced by spinal intrathecal injection of FeCl2 (mouse-FeCl2-it assay) in vivo. Selected compounds were tested for antagonistic activity on methamphetamine (MAP)-induced hypermotility resulting from dopamine release in the mouse brain. Among the compounds synthesized, compound 26n (2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)meth]-5-benzofuranamine) exhibited potent effects in these assays (inhibition of lipid peroxidation, IC50 = 0.07 mu M; mouse-FeCl2-it assay, ID50 = 10.4 mg/kg, po; MAP-induced hypermotility, 98% inhibition, 10 mg/kg, ip). The S-(+)-form of compound 26n dihydrochloride (TAK-218), which has 30 times more potent antagonistic activity on MAP-induced hypermotility than the R-(-)-form, improved more significantly the survival rate in the cerebral ischemia model (rat, 1-3 mg/kg, ip) during the period of 1-14 days after ischemia and decreased functional disorders in the traumatic brain injury model (rat, 0.1-1 mg/kg, ip) 3-14 days after injury. These results imply a role for dopamine in deterioration of CNS function after ischemic and traumatic injury. TAK-218 is a promising compound for the treatment of stroke and CNS trauma and is now under clinical investigation.

  DOI：

  10.1021/jm960411j

文献信息

• 4-AMINO-7,8-DIHYDROPYRIDO[4,3-d]PYRIMIDIN-5(6H)-ONE DERIVATIVES
  申请人：Aspnes Gary E.

  公开号：US20100197591A1

  公开（公告）日：2010-08-05

  The invention provides compounds of the general Formula (I) where R 1 , R 2 , and A are defined herein, as well as the preparation, compositions and uses thereof.

  这项发明提供了一般式（I）的化合物 其中R1、R2和A在此处定义，以及其制备、组成和用途。
• Azo dyestuffs from 5-amino coumaran
  申请人：AMERICAN CYANAMID CO

  公开号：US02383264A1

  公开（公告）日：1945-08-21
• DUGGAN, ANGELINA J.
  作者：DUGGAN, ANGELINA J.

  DOI：——

  日期：——
• KITO, OIDZO;TAMURA, MASAKI;IKEHDZAVA, SEHJDZO
  作者：KITO, OIDZO、TAMURA, MASAKI、IKEHDZAVA, SEHJDZO

  DOI：——

  日期：——
• [EN] QUINOLINAMINE COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF IN PHARMACEUTICALS<br/>[FR] COMPOSÉ QUINOLINAMINE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION DANS DES PRODUITS PHARMACEUTIQUES<br/>[ZH] 喹啉胺类化合物、其制备方法及其在医药上的应用
  申请人：JIANGSU HENGRUI PHARMACEUTICALS CO LTD

  公开号：WO2022247920A9

  公开（公告）日：2023-01-05