7-chloro-8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine | 107128-79-0

• 物质功能分类: 分析化学 - 标准品 - 法医和兽医标准品
• 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-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• 英文别名: SCH23390；8-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol
• CAS: 107128-79-0
• 化学式: C₁₆H₁₆ClNO
• 分子量: 273.762
• InChiKey: ZVKJSJAERRMBMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  7-chloro-8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 生成 7-Chloro-3-methyl-1-phenyl-1,2,4,5-tetrahydro-3-benzazepin-8-ol
  参考文献：
  名称：

  DEJESUS O. T.; WOOLVERTON W. L.; VAN MOFFAERT G. J. C.; COOPER M. D.; FRI+, J. LABELLED COMPOUNDS AND RADIOPHARM., 23,(1986) N 10-12, 1403-1404

  摘要：

  DOI：

文献信息

• (.+-.)-3-Allyl-7-halo-8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines as selective high affinity D1 dopamine receptor antagonists: synthesis and structure-activity relationship
  作者：Nandkishore Baindur、Mai Tran、Hyman B. Niznik、H. C. Guan、Phillip Seeman、John L. Neumeyer

  DOI：10.1021/jm00079a008

  日期：1992.1

  Substituted 1-phenyl-3-benzazepines form a class of compounds possessing potent and selective affinity for the D1 DA receptor. 7,8-Dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (SKF 38393) and its 6-halo analogues are potent and selective D1 receptor agonists. Recently, the 3-allyl derivatives of SKF 38393 and its analogues were described as selective D1 agonists with higher D1 efficacy and CNS potency. In order to extend these results to compounds in the 7-halo-8-hydroxy-substituted antagonist series, we have synthesized and pharmacologically characterized 3-allyl analogues of 7-substituted (Cl, Br, H) 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines. These 3-allyl derivatives were compared with their 3-methyl and 3-unsubstituted analogues in terms of their D1 receptor affinity and selectivity. The results have been used to generate structure-affinity relationships. The D1 receptor affinity, for 3-substitution, is found to be in the order: methyl > allyl > H. For 7-substitution, the affinity is in the order: Cl = Br > H. The 3-allyl compounds show affinity close to that of the parent (3-methyl) compounds while exhibiting a slightly diminished D1 selectivity. However, the greater lipophilicity of the 3-allyl compounds may enable them to cross the blood-brain barrier more readily and thereby exhibit higher in vivo CNS potency. Thus 3-allylbenzazepines have potential as high affinity selective Dl antagonists.
• WYRICK S. D.; MCDOUGALD D. L.; MAILMAN R. B., J. LABELLED COMPOUNDS AND RADIOPHARM., 23,(1986) N 7, 685-692
  作者：WYRICK S. D.、 MCDOUGALD D. L.、 MAILMAN R. B.

  DOI：——

  日期：——
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  申请人：Weinstock Joseph

  公开号：US20100316731A1

  公开（公告）日：2010-12-16

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  公开号：US20140316130A1

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  申请人：PSYADON PHARMACEUTICALS, INC.

  公开号：US20150164911A1

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