3-methyl-5-phenyl-2,3,4,5-tetrahydro-benzo[d]azepin-7-amine | 1564256-53-6

• 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: 3-methyl-5-phenyl-2,3,4,5-tetrahydro-benzo[d]azepin-7-amine
• 英文别名: 8-amino-3-methyl-1-phenyl-benzazepine；3-Methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-amine；3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-amine
• CAS: 1564256-53-6
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: JNDPGFKINLFTLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3-methyl-5-phenyl-2,3,4,5-tetrahydro-benzo[d]azepin-7-amine 在 甲酸 作用下， 以18%的产率得到8-(N,N-dimethylamino)-3-methyl-1-phenyl-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
• 作为产物：
  描述：

  3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl trifluoromethanesulfonate 在 18-冠醚-6 、 盐酸羟胺 、 sodium acetate 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 3-methyl-5-phenyl-2,3,4,5-tetrahydro-benzo[d]azepin-7-amine
  参考文献：
  名称：

  Novel 2,4-Diarylaminopyrimidine Analogues (DAAPalogues) Showing Potent c-Met/ALK Multikinase Inhibitory Activities

  摘要：

  By repurposing a typical dopamine D-1/D-5 receptor agonist motif, C1-substituted-N3-benzazepine or benzazecine, into the classical RTK inhibitor 2,4-diaminopyrimidine skeleton, a series of new 2,4-diarylaminopyrimidine analogues (DAAPalogues) were developed. Compounds 7 and 8a were identified possessing high potency against both c-Met and ALK kinases. Compound 8a displayed appreciable antitumor efficacy at the dose of 1 mg/kg in the ALK-driven BF3/EML4-ALK xenograft mice model.

  DOI：

  10.1021/ml400373j