1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] | 69585-10-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine]
• 英文别名: 1-(2-chlorophenyl)-1'-methylspiro[2H-indole-3,4'-piperidine]
• CAS: 69585-10-0
• 化学式: C₁₉H₂₁ClN₂
• 分子量: 312.842
• InChiKey: FCOKTVVKRPCHAN-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：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine] 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-(2-chlorophenyl)spiro[2H-indole-3,4'-piperidine]
  参考文献：
  名称：

  Novel tetracyclic spiropiperidines. 3. 1-Arylspiro[indoline-3,4'-piperidine]s as potential antidepressants

  摘要：

  A series of 1-arylspiro[indoline-3,4'-piperidine]s was synthesized and evaluated for potential antidepressant activity by tetrabenazine (TBZ) ptosis prevention and potentiation of 5-hydroxytryptophan (5-HTP) induced head twitching in pargyline-pretreated rats. Marked TBZ activity was observed with analogues bearing an ortho substituent on the pendant aromatic ring, as exemplified by lead compound 25a, 1-(2-chlorophenyl)spiro[indoline-3,4'-piperidine], which was also very active in potentiating 5-HTP stereotypy and yohimbine toxicity, as well as in inhibiting the muricidal behavior in rats. The potent in vivo activity of 25a, coupled with weak to moderate in vitro activity with respect to the blockade of neuronal reuptake of biogenic amines, seems to suggest a profile atypical of tricyclic antidepressants.

  DOI：

  10.1021/jm00361a009
• 作为产物：
  描述：

  恩比兴 在 lithium aluminium tetrahydride 、 sodium hydride 、 lithium triethoxyaluminum hydride 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 80.5h， 生成 1-(2-chlorophenyl)-1'-methylspiro[indoline-3,4'-piperidine]
  参考文献：
  名称：

  Novel tetracyclic spiropiperidines. 3. 1-Arylspiro[indoline-3,4'-piperidine]s as potential antidepressants

  摘要：

  A series of 1-arylspiro[indoline-3,4'-piperidine]s was synthesized and evaluated for potential antidepressant activity by tetrabenazine (TBZ) ptosis prevention and potentiation of 5-hydroxytryptophan (5-HTP) induced head twitching in pargyline-pretreated rats. Marked TBZ activity was observed with analogues bearing an ortho substituent on the pendant aromatic ring, as exemplified by lead compound 25a, 1-(2-chlorophenyl)spiro[indoline-3,4'-piperidine], which was also very active in potentiating 5-HTP stereotypy and yohimbine toxicity, as well as in inhibiting the muricidal behavior in rats. The potent in vivo activity of 25a, coupled with weak to moderate in vitro activity with respect to the blockade of neuronal reuptake of biogenic amines, seems to suggest a profile atypical of tricyclic antidepressants.

  DOI：

  10.1021/jm00361a009

文献信息

• Process for preparing spiro[indoline-3,4'-piperidine]s
  申请人：American Hoechst Corporation

  公开号：US04379932A1

  公开（公告）日：1983-04-12

  Novel spiro[indoline-3,4'-piperidine]s and related compounds and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants and tranquilizers. Also described is a novel method of preparing indoline rings.

  本发明涉及新型螺环[吲哚啉-3,4'-哌啶]和相关化合物以及其制备方法。这些化合物可用作抗抑郁、抗癫痫和镇静剂。还描述了一种新型吲哚啉环的制备方法。
• US4209625A
  申请人：——

  公开号：US4209625A

  公开（公告）日：1980-06-24
• US4307235A
  申请人：——

  公开号：US4307235A

  公开（公告）日：1981-12-22
• US4345081A
  申请人：——

  公开号：US4345081A

  公开（公告）日：1982-08-17
• US4379932A
  申请人：——

  公开号：US4379932A

  公开（公告）日：1983-04-12