2a-(4-Bromobutyl)-6-chloro-1,3,4,5-tetrahydrobenzo[cd]indol-2-one | 402942-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2a-(4-Bromobutyl)-6-chloro-1,3,4,5-tetrahydrobenzo[cd]indol-2-one
• 英文别名: 2a-(4-bromobutyl)-6-chloro-1,3,4,5-tetrahydrobenzo[cd]indol-2-one
• CAS: 402942-69-2
• 化学式: C₁₅H₁₇BrClNO
• 分子量: 342.663
• InChiKey: OSAIRNVJVNRECU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(4-氟苯基)-1,2,3,6-四氢吡啶 、 2a-(4-Bromobutyl)-6-chloro-1,3,4,5-tetrahydrobenzo[cd]indol-2-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到6-chloro-2a-[4-[4-(4-fluorophenyl)-3,6-dihydro-2H-pyridin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one
  参考文献：
  名称：

  New tetrahydrobenzindoles as potent and selective 5-HT7 antagonists with increased In vitro metabolic stability

  摘要：

  Chemical modifications of compound 1 (DR4004), a potent, selective antagonist of the 5-HT7 receptor, were conducted with the aim of improving its metabolic stability. Halogenation of putative sites of oxidative metabolism afforded compounds 7-10, which retained high affinity and selectivity for the 5-HT7 receptor, and showed increased in vitro metabolic stability. Compound 10 (DR4485) showed oral bioavailability, and should be a useful tool for evaluating the therapeutic potential of 5-HT7 antagonists. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00842-9
• 作为产物：
  描述：

  2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到2a-(4-Bromobutyl)-6-chloro-1,3,4,5-tetrahydrobenzo[cd]indol-2-one
  参考文献：
  名称：

  New tetrahydrobenzindoles as potent and selective 5-HT7 antagonists with increased In vitro metabolic stability

  摘要：

  Chemical modifications of compound 1 (DR4004), a potent, selective antagonist of the 5-HT7 receptor, were conducted with the aim of improving its metabolic stability. Halogenation of putative sites of oxidative metabolism afforded compounds 7-10, which retained high affinity and selectivity for the 5-HT7 receptor, and showed increased in vitro metabolic stability. Compound 10 (DR4485) showed oral bioavailability, and should be a useful tool for evaluating the therapeutic potential of 5-HT7 antagonists. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00842-9