7-(p-hydroxyphenyl)-3-methyl-1-phenyl-8-hydroxy-benzazepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-(p-hydroxyphenyl)-3-methyl-1-phenyl-8-hydroxy-benzazepine
• 英文别名: 8-(4-Hydroxyphenyl)-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol；8-(4-hydroxyphenyl)-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: MQNXSZOCUGNTGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-7-bromo-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 在 potassium phosphate 、 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 甲酸 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 7-(p-hydroxyphenyl)-3-methyl-1-phenyl-8-hydroxy-benzazepine
  参考文献：
  名称：

  Structural manipulation on the catecholic fragment of dopamine D1 receptor agonist 1-phenyl-N-methyl-benzazepines

  摘要：

  A series of new benzazepines with modification on the catecholic fragment were designed. The 8-hydroxyl group, other than the 7-hydroxyl was confirmed crucial to the interaction with the dopamine D-1 receptor. Subsequent replacement of the 7-hydroxyl with benzylamino groups was found tolerable. 7-(m-Chlorophenyl)methylamino- and 7-(m- or o-tolyl)methylamino-substituted benzazepines 13b-d displayed K-i values of 270-370 nM at the D-1 receptor, which were slightly more potent than that of parent compound I. In addition, 7-(arylmethyl)amino-benzazepines 13a-c were found possessing high binding affinities less than 10 nM at the 5-HT2A receptor. Among them, the non-substituted 7-benzylamino analogue 13a was the most potent showing a K-i values of 4.5 nM at the 5-HT2A receptor and a 5-HT2A/D-1 selectivity of 147. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.059

文献信息

• Structural manipulation on the catecholic fragment of dopamine D1 receptor agonist 1-phenyl-N-methyl-benzazepines
  作者：Jing Zhang、Jiye Huang、Zilan Song、Lin Guo、Wenxian Cai、Yun Wang、Xuechu Zhen、Ao Zhang

  DOI：10.1016/j.ejmech.2014.07.059

  日期：2014.10

  A series of new benzazepines with modification on the catecholic fragment were designed. The 8-hydroxyl group, other than the 7-hydroxyl was confirmed crucial to the interaction with the dopamine D-1 receptor. Subsequent replacement of the 7-hydroxyl with benzylamino groups was found tolerable. 7-(m-Chlorophenyl)methylamino- and 7-(m- or o-tolyl)methylamino-substituted benzazepines 13b-d displayed K-i values of 270-370 nM at the D-1 receptor, which were slightly more potent than that of parent compound I. In addition, 7-(arylmethyl)amino-benzazepines 13a-c were found possessing high binding affinities less than 10 nM at the 5-HT2A receptor. Among them, the non-substituted 7-benzylamino analogue 13a was the most potent showing a K-i values of 4.5 nM at the 5-HT2A receptor and a 5-HT2A/D-1 selectivity of 147. (C) 2014 Elsevier Masson SAS. All rights reserved.