2-(6-chlorospiro[2H-indole-3,4'-piperidine]-1-yl)aniline | 75391-92-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(6-chlorospiro[2H-indole-3,4'-piperidine]-1-yl)aniline
• CAS: 75391-92-3
• 化学式: C₁₈H₂₀ClN₃
• 分子量: 313.83
• InChiKey: ARBGQJLPNKIZKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-2-氟苯乙腈 在 盐酸 、 lithium aluminium tetrahydride 、 铁粉 、 sodium hydride 、 potassium carbonate 、 lithium triethoxyaluminum hydride 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 100.5h， 生成 2-(6-chlorospiro[2H-indole-3,4'-piperidine]-1-yl)aniline
  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