[(5R)-8-chloro-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl] 4-nitrobenzoate | 1215022-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(5R)-8-chloro-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl] 4-nitrobenzoate
• CAS: 1215022-46-0
• 化学式: C₂₄H₂₁ClN₂O₄
• 分子量: 436.895
• InChiKey: KRNBRRIVRFYUII-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(5R)-8-chloro-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl] 4-nitrobenzoate 在 溴 、 mercury(II) trifluoroacetate 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以25%的产率得到[(5R)-5-(4-bromophenyl)-8-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl] 4-nitrobenzoate
  参考文献：
  名称：

  Selective D1/D5 receptor antagonists for the treatment of obesity and CNS disorders

  摘要：

  本发明提供了一种新型D1/D5受体拮抗剂化合物，以及制备这种化合物的方法。在另一实施方式中，该发明提供了包含这种D1/D5受体拮抗剂的药物组合物，以及使用它们来治疗中枢神经系统疾病、肥胖症、代谢性疾病、食欲紊乱疾病（如暴食症）和糖尿病的方法。

  公开号：

  US20050075325A1
• 作为产物：
  描述：

  SCH 23390 、 4-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到[(5R)-8-chloro-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl] 4-nitrobenzoate
  参考文献：
  名称：

  Discovery of new SCH 39166 analogs as potent and selective dopamine D1 receptor antagonists

  摘要：

  A series of novel dopamine D-1 antagonists derived from functionalization of the D-ring of SCH 39166 were prepared. A number of these compounds displayed subnanomolar D-1 activity and more than 1000-fold selectivity over D-2. We found C-3 derivatization afforded compounds with superior overall pro. le in comparison to the C-2 and C-4 derivatization. A number of highly potent D-1 antagonists were discovered which have excellent selectivity over other dopamine receptors and improved PK pro. le compared to SCH 39166. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.100

文献信息

• US7504391B2
  申请人：——

  公开号：US7504391B2

  公开（公告）日：2009-03-17
• Selective D1/D5 receptor antagonists for the treatment of obesity and CNS disorders
  申请人：Burnett A. Duane

  公开号：US20050075325A1

  公开（公告）日：2005-04-07

  The present invention provides compounds, which, are novel antagonists for D 1 /D 5 receptors as well as methods for preparing such compounds. In another embodiment, the invention provides pharmaceutical compositions comprising such D 1 /D 5 receptor antagonists as well as methods of using them to treat CNS disorders, obesity, metabolic disorders, eating disorders such as hyperphagia, and diabetes.

  本发明提供了一种新型D1/D5受体拮抗剂化合物，以及制备这种化合物的方法。在另一实施方式中，该发明提供了包含这种D1/D5受体拮抗剂的药物组合物，以及使用它们来治疗中枢神经系统疾病、肥胖症、代谢性疾病、食欲紊乱疾病（如暴食症）和糖尿病的方法。
• Discovery of new SCH 39166 analogs as potent and selective dopamine D1 receptor antagonists
  作者：Li Qiang、T.K. Sasikumar、Duane A. Burnett、Jing Su、Haiqun Tang、Yuanzan Ye、Robert D. Mazzola、Zhaoning Zhu、Brian A. McKittrick、William J. Greenlee、Ahmad Fawzi、Michelle Smith、Hongtao Zhang、Jean E. Lachowicz

  DOI：10.1016/j.bmcl.2009.12.100

  日期：2010.2

  A series of novel dopamine D-1 antagonists derived from functionalization of the D-ring of SCH 39166 were prepared. A number of these compounds displayed subnanomolar D-1 activity and more than 1000-fold selectivity over D-2. We found C-3 derivatization afforded compounds with superior overall pro. le in comparison to the C-2 and C-4 derivatization. A number of highly potent D-1 antagonists were discovered which have excellent selectivity over other dopamine receptors and improved PK pro. le compared to SCH 39166. (C) 2009 Elsevier Ltd. All rights reserved.