1,3-dihydro-3-(2-methylphenyl)spiro[benzo(c)thiophene-1,4'-piperidine] | 72364-55-7

• 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: 1,3-dihydro-3-(2-methylphenyl)spiro[benzo(c)thiophene-1,4'-piperidine]
• 英文别名: 1-(2-methylphenyl)spiro[1H-2-benzothiophene-3,4'-piperidine]
• CAS: 72364-55-7
• 化学式: C₁₉H₂₁NS
• 分子量: 295.448
• InChiKey: AVHOXQCHMJKTJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-3-(2-methylphenyl)spiro[benzo(c)thiophene-1,4'-piperidine] 生成 1'-[3-(4-fluorobenzoyl)propyl]-1,3-dihydro-3-(2-methylphenyl)spiro[benzo(c)thiophene-1,4'-piperidine]
  参考文献：
  名称：

  ONG, H. H.;ANDERSON, V. B.;PROFITT, J. A.

  摘要：

  DOI：
• 作为产物：
  描述：

  邻溴氟苯 在 氢氧化钾 、 正丁基锂 、 三氟化硼 、 碳酸氢钠 、 dimsyl sodium 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙二醇 、 二甲基亚砜 为溶剂， 反应 21.5h， 生成 1,3-dihydro-3-(2-methylphenyl)spiro[benzo(c)thiophene-1,4'-piperidine]
  参考文献：
  名称：

  Novel tetracyclic spiropiperidines. 1. 3-Aryl-1,3-dihydrospiro[benzo[c]thiophene-1,4'-piperidines] as potential antidepressants

  摘要：

  A series of 3-aryl-1,3-dihydrospiro[benzo[c]thiophene-1,4'-piperidine] derivatives was synthesized and evaluated pharmacologically for potential psychotropic activity. Potent antidepressant-like activity was noted throughout the series, as assessed by tetrabenazine (TBZ) ptosis prevention in mice and potentiation of 5-hydroxytryptophan (5-HTP) induced behavioral effects in rats. A possible therapeutic advantage of the title compounds appears to be the overall low anticholinergic potential in comparison with the classic tricyclic antidepressants. Several congeners with nuclear halogen substitution also exhibited CNS stimulant properties, as evidenced by their ability to induce a dopamine agonist-like stereotypy and to increase the spontaneous motor activity in mice.

  DOI：

  10.1021/jm00133a016

文献信息

• ONG, H. H.;ANDERSON, V. B.;PROFITT, J. A.
  作者：ONG, H. H.、ANDERSON, V. B.、PROFITT, J. A.

  DOI：——

  日期：——
• Substituierte 1,3-Dihydrospiro (benzo(c)thiophene), Verfahren zu deren Herstellung und diese Verbindungen zur Verwendung als Arzneimittel
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0002283B1

  公开（公告）日：1983-08-24
• US4409229A
  申请人：——

  公开号：US4409229A

  公开（公告）日：1983-10-11
• Novel tetracyclic spiropiperidines. 1. 3-Aryl-1,3-dihydrospiro[benzo[c]thiophene-1,4'-piperidines] as potential antidepressants
  作者：Helen H. Ong、James A. Profitt、V. Brian Anderson、Hansjoerg Kruse、Jeffrey C. Wilker、Harry M. Geyer

  DOI：10.1021/jm00133a016

  日期：1981.1

  A series of 3-aryl-1,3-dihydrospiro[benzo[c]thiophene-1,4'-piperidine] derivatives was synthesized and evaluated pharmacologically for potential psychotropic activity. Potent antidepressant-like activity was noted throughout the series, as assessed by tetrabenazine (TBZ) ptosis prevention in mice and potentiation of 5-hydroxytryptophan (5-HTP) induced behavioral effects in rats. A possible therapeutic advantage of the title compounds appears to be the overall low anticholinergic potential in comparison with the classic tricyclic antidepressants. Several congeners with nuclear halogen substitution also exhibited CNS stimulant properties, as evidenced by their ability to induce a dopamine agonist-like stereotypy and to increase the spontaneous motor activity in mice.