4-(7-benzyloxy-1-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-yl)-1-(4-tert-butylphenyl)butane-1-one | 1253197-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(7-benzyloxy-1-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-yl)-1-(4-tert-butylphenyl)butane-1-one
• 英文别名: (+/-)-4-(7-benzyloxy-1-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)-1-(4-tert-butylphenyl)butan-1-one；1-(4-Tert-butylphenyl)-4-(5-hydroxy-8-phenylmethoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)butan-1-one
• CAS: 1253197-44-2
• 化学式: C₃₁H₃₇NO₃
• 分子量: 471.64
• InChiKey: IHILJRZZZCWCMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-(benzyloxy)-3-{3-[2-(4-tert-butylphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]propyl}-2,3,4,5-tetrahydro-1H-3-benzazepine-1-ol 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 16.0h， 生成 4-(7-benzyloxy-1-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-yl)-1-(4-tert-butylphenyl)butane-1-one
  参考文献：
  名称：

  [EN] NR2B-SELECTIVE NMDA-RECEPTOR ANTAGONISTS
  [FR] ANTAGONISTES DES RÉCEPTEURS NMDA SÉLECTIFS DU SITE NR2B

  摘要：

  本发明涉及符合一般式（I）的化合物以及包含符合一般式（I）的化合物的药物组合物。

  公开号：

  WO2010122134A1

文献信息

• [EN] NR2B SELECTIVE NMDA-RECEPTOR ANTAGONISTS FOR TREATMENT OF IMMUNE-MEDIATED INFLAMMATORY DISEASES<br/>[FR] ANTAGONISTES DU RÉCEPTEUR NMDA SÉLECTIFS DE NR2B POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES À MÉDIATION IMMUNITAIRE
  申请人：WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTER

  公开号：WO2017036880A1

  公开（公告）日：2017-03-09

  The present invention provides novel means and methods for treatment auf immunemediated inflammatory diseases.

  本发明提供了治疗免疫介导性炎症性疾病的新手段和方法。
• NR2B-selective NMDA-receptor antagonists
  申请人：Westfälische Wilhelms-Universität Münster

  公开号：EP2246331A1

  公开（公告）日：2010-11-03

  The present invention relates to NMDA antagonists that target the NR2B subunit according to general formula (I) and pharmaceutical compositions comprising compounds according to general formula (I).

  本发明涉及根据通式（I）靶向 NR2B 亚基的 NMDA 拮抗剂和包含根据通式（I）化合物的药物组合物。
• Conformationally constrained NR2B selective NMDA receptor antagonists derived from ifenprodil: Synthesis and biological evaluation of tetrahydro-3-benzazepine-1,7-diols
  作者：Bastian Tewes、Bastian Frehland、Dirk Schepmann、Kai-Uwe Schmidtke、Thomas Winckler、Bernhard Wünsch

  DOI：10.1016/j.bmc.2010.09.026

  日期：2010.11.15

  NR2B selective NMDA receptor antagonists with tetrahydro-3-benzazepine-1,7-diol scaffold have been designed by formal cleavage and reconstitution of the piperidine ring of the lead compound ifenprodil (1). The secondary amine 10 represents the central building block for the synthesis of more than 25 tetrahydro-3-benzazepin-1-ols. Generally 7-hydroxy derivatives display higher NR2B receptor affinities than the corresponding 7-benzyloxy compounds. A distance of four atoms (five bond lengths) between the basic amino group and the terminal aryl moiety led to highest NR2B affinity. 3-(4-Phenylbutyl)-2,3,4,5- tetrahydro-1H-3-benzazepine-1,7-diol (WMS-1410, 25) represents the most promising NR2B antagonist of this series showing a K-i-value of 14 nM. Compound 25 reveals excellent selectivity over more than 100 further relevant target proteins, antagonizes glutamate induced excitotoxicity (IC50 = 18.4 nM) and is metabolically more stable than ifenprodil. Up to a dose of 100 mg/kg 25 is well tolerated by mice and it shows dose dependent analgesic activity in the late neuropathic pain phase of the formalin assay. (C) 2010 Elsevier Ltd. All rights reserved.
• NR2B SELECTIVE NMDA-RECEPTOR ANTAGONISTS FOR TREATMENT OF IMMUNE-MEDIATED INFLAMMATORY DISEASES
  申请人：Westfälische Wilhelms-Universität Münster

  公开号：EP3344257A1

  公开（公告）日：2018-07-11