6-chloro-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine | 461435-44-9

• 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: 6-chloro-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• 英文别名: 6-chloro-7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS: 461435-44-9
• 化学式: C₁₀H₁₁ClN₂O₂
• 分子量: 226.663
• InChiKey: NDFYZOYUHRVRJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-chloro-3-methyl-7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine 在 1-氯乙基氯甲酸酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以53%的产率得到6-chloro-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a series of benzazepine derivatives as 5-HT2C receptor agonists

  摘要：

  To identify potent and selective 5-HT2C receptor agonists, a series of novel benzazepine derivatives were synthesized, and their structure-activity relationships examined. The compounds were evaluated for their 5-HT2C, 5-HT2A, and 5-HT2B receptor binding affinity and intrinsic activity for the 5-HT2C and 5-HT2A receptors. Among these compounds, 6,7-dichloro-2,3,4,5-tetrahydro-1H-3-benzazepine (6) was effective in a rat penile erection model when administered po, which is a symptom of the serotonin syndrome reflecting 5-HT2C receptor activation. Moreover, compound 6 was characterized as a partial agonist of 5-HT2A receptors; therefore, it had little effect on the cardiovascular system. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.009

文献信息

• Synthesis and structure–activity relationships of a series of benzazepine derivatives as 5-HT2C receptor agonists
  作者：Itsuro Shimada、Kyoichi Maeno、Yutaka Kondoh、Hidetaka Kaku、Keizo Sugasawa、Yasuharu Kimura、Ken-ichi Hatanaka、Yuki Naitou、Fumikazu Wanibuchi、Shuichi Sakamoto

  DOI：10.1016/j.bmc.2007.12.009

  日期：2008.3.15

  To identify potent and selective 5-HT2C receptor agonists, a series of novel benzazepine derivatives were synthesized, and their structure-activity relationships examined. The compounds were evaluated for their 5-HT2C, 5-HT2A, and 5-HT2B receptor binding affinity and intrinsic activity for the 5-HT2C and 5-HT2A receptors. Among these compounds, 6,7-dichloro-2,3,4,5-tetrahydro-1H-3-benzazepine (6) was effective in a rat penile erection model when administered po, which is a symptom of the serotonin syndrome reflecting 5-HT2C receptor activation. Moreover, compound 6 was characterized as a partial agonist of 5-HT2A receptors; therefore, it had little effect on the cardiovascular system. (C) 2007 Elsevier Ltd. All rights reserved.