3-(3,4-dichlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine] | 72364-18-2

• 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: 3-(3,4-dichlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine]
• 英文别名: 1-(3,4-dichlorophenyl)-1'-methylspiro[1H-2-benzothiophene-3,4'-piperidine]
• CAS: 72364-18-2
• 化学式: C₁₉H₁₉Cl₂NS
• 分子量: 364.339
• InChiKey: MDFWWOQSMCSSKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 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：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine] 在 氢氧化钾 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙二醇 为溶剂， 反应 4.5h， 生成 base 3-(3,4-dichlorophenyl)-1,3-dihydrospiro[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
• 作为产物：
  描述：

  邻溴氟苯 在 正丁基锂 、 三氟化硼 、 dimsyl sodium 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 生成 3-(3,4-dichlorophenyl)-1,3-dihydro-1'-methylspiro[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

• Antidepressive and tranquilizing substituted
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04409229A1

  公开（公告）日：1983-10-11

  Novel substituted 1,3-dihydrospiro[benzo(c)thiophene]s and methods of preparing the same are described. These compounds are useful as antidepressants and tranquilizers and intermediates therefor.

  本发明描述了替代1,3-二氢螺[苯并(c)噻吩]的小说化合物及其制备方法。这些化合物可用作抗抑郁药和镇静剂及其中间体。
• Process for preparing substituted 1,3-dihydrospiro[benzo(c)thiophene]s
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04524207A1

  公开（公告）日：1985-06-18

  Novel substituted 1,3-dihydrospiro[benzo(c)thiophene]s and methods of preparing the same are described. These compounds are useful as antidepressants and tranquilizers and intermediates therefor.

  本发明涉及代替1,3-二氢螺[苯并(c)噻吩]的新型化合物及其制备方法。这些化合物可用作抗抑郁剂和镇静剂，也可作为其中间体。
• 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
• US4524207A
  申请人：——

  公开号：US4524207A

  公开（公告）日：1985-06-18