7-chloro-8-hydroxy-1-(4'-iodophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine | 120685-93-0

• 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-chloro-8-hydroxy-1-(4'-iodophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• 英文别名: 8-Chloro-5-(4-iodophenyl)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol
• CAS: 120685-93-0
• 化学式: C₁₇H₁₇ClINO
• 分子量: 413.686
• InChiKey: SFEBAZSWFKLMDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-chloro-8-methoxy-1-(4'-bromophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine 在 三溴化硼 作用下， 以 甲酸 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 7-chloro-8-hydroxy-1-(4'-iodophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  (.+-.)-7-Chloro-8-hydroxy-1-(4'-[125I]iodophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine: a potential CNS D-1 dopamine receptor imaging agent

  摘要：

  Synthesis, radiolabeling, and in vitro and in vivo properties of an iodinated benzazepine, (+/-)-7-chloro-8-hydroxy-1-(4'-[125I]iodophenyl)-3- methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, [125I]FISCH, as a potential imaging agent for evaluation of central nervous system (CNS) D-1 dopamine receptors in humans, were investigated. After an iv injection, this benzazepine derivative showed good brain uptake in rats (2.27, 1.40, 0.55% dose/whole brain at 2, 15, and 60 min, respectively). The striatum/cerebellum ratio was high (2.47 at 60 min after the injection). The binding affinity of this agent in rat striatum tissue preparation displayed a Kd of 1.43 +/- 0.15 nM. Competition data (in vitro) showed the following rank order of potency: SCH-23390 greater than (+/-)-FISCH greater than (+/-)-IBZP much greater than apomorphine greater than WB 4010 greater than ketanserin approximately spiperone. The preliminary data suggest that the agent is highly selective for the CNS D-1 receptor.

  DOI：

  10.1021/jm00127a005

文献信息

• CHUMPRADIT, SUMALEE;KUNG, HANK F.;BILLINGS, JEFFREY;KUNG, MEI-PING;PAN, S+, J. MED. CHEM., 32,(1989) N, C. 1431-1435
  作者：CHUMPRADIT, SUMALEE、KUNG, HANK F.、BILLINGS, JEFFREY、KUNG, MEI-PING、PAN, S+

  DOI：——

  日期：——
• Dopamine receptor ligands and imaging agents
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：EP0391554B1

  公开（公告）日：1997-09-10
• US5130117A
  申请人：——

  公开号：US5130117A

  公开（公告）日：1992-07-14
• (.+-.)-7-Chloro-8-hydroxy-1-(4'-[125I]iodophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine: a potential CNS D-1 dopamine receptor imaging agent
  作者：Sumalee Chumpradit、Hank F. Kung、Jeffrey Billings、Mei Ping Kung、Sangren Pan

  DOI：10.1021/jm00127a005

  日期：1989.7

  Synthesis, radiolabeling, and in vitro and in vivo properties of an iodinated benzazepine, (+/-)-7-chloro-8-hydroxy-1-(4'-[125I]iodophenyl)-3- methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, [125I]FISCH, as a potential imaging agent for evaluation of central nervous system (CNS) D-1 dopamine receptors in humans, were investigated. After an iv injection, this benzazepine derivative showed good brain uptake in rats (2.27, 1.40, 0.55% dose/whole brain at 2, 15, and 60 min, respectively). The striatum/cerebellum ratio was high (2.47 at 60 min after the injection). The binding affinity of this agent in rat striatum tissue preparation displayed a Kd of 1.43 +/- 0.15 nM. Competition data (in vitro) showed the following rank order of potency: SCH-23390 greater than (+/-)-FISCH greater than (+/-)-IBZP much greater than apomorphine greater than WB 4010 greater than ketanserin approximately spiperone. The preliminary data suggest that the agent is highly selective for the CNS D-1 receptor.