base 3-(2-chlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine] | 72364-44-4

• 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: base 3-(2-chlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine]
• 英文别名: 3-(2-Chlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine]；1-(2-chlorophenyl)-1'-methylspiro[1H-2-benzothiophene-3,4'-piperidine]
• CAS: 72364-44-4
• 化学式: C₁₉H₂₀ClNS
• 分子量: 329.894
• InChiKey: OQUABUJYMPEQKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 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：

  base 3-(2-chlorophenyl)-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 3-(2-chlorophenyl)-1,3-dihydro-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
• 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 base 3-(2-chlorophenyl)-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。
• 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：EP0002283A1

  公开（公告）日：1979-06-13

  Verbindungen der Formel .worin R für Wasserstoff, Hydroxyl, Benzoyloxy, Niederalkyl, Cycloalkylniederalkyl oder Cycloalkylniederalkanoyl, Niederalkenyl, Phenylniederalkyl, Diphenylniederalkyl, Diphenyl- . methoxyniederalkyl, Phenoxyniederalkyl, Alkanoyl, Phenylalkanoyl, Benzoyl, Benzoylniederalkyl, Phenylhydroxyniederalkyl, Alkoxycarbonyl, Phenoxycarbonyl, Cycloalkylcarbonyl bonyl oder wobei Ph Phenyl darstellt, steht, R' und R2 gleich oder verschieden sind und je für Wasserstoff, Niederalkyl, Niederalkoxy, Trifluormethyl, Chlor, Brom, Fluor, Hydroxyl, Methylendioxy oder Niederalkylthio stehen können m, n und n' ganze Zahlen von 1 bis 3 bedeuten und die Summe von n und n' 3 oder 4 ist, welche als Antidepressive nützlich sind.

  式中的化合物 其中 R 是氢、羟基、苯甲酰氧基、低级烷基、环烷基-低级烷基或环烷基-低级烷酰基、低级烯基、苯基-低级烷基、二苯基-低级烷基、二苯基-.甲氧基-低级烷基、苯氧基-低级烷基、烷酰基、苯基烷酰基、苯甲酰基、苯甲酰基-低级烷基、苯基羟基-低级烷基、烷氧基羰基、苯氧基羰基、环烷基羰基羰基，或 其中 Ph 为苯基，R'和 R2 相同或不同，且各自为氢、低级烷基、低级烷氧基、三氟甲基、氯、溴、氟、羟基、亚甲基二氧基或低级烷硫基，m、n 和 n' 为 1 至 3 的整数，且 n 和 n' 之和为 3 或 4，可用作抗抑郁剂。
• 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
• 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.