5-(2-chloroacetyl)spiro[1H-indole-3,1'-cyclopentane]-2-one | 118307-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(2-chloroacetyl)spiro[1H-indole-3,1'-cyclopentane]-2-one
• CAS: 118307-00-9
• 化学式: C₁₄H₁₄ClNO₂
• 分子量: 263.724
• InChiKey: PBQAEYXFWJEIOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-chloroacetyl)spiro[1H-indole-3,1'-cyclopentane]-2-one 在 三乙基硅烷 、 三氟乙酸 作用下， 生成 5'-(2-chloroethyl)-spiro[cyclopentane-1,3'-indoline]-2'-one
  参考文献：
  名称：

  3-Benzisothiazolylpiperazine Derivatives as Potential Atypical Antipsychotic Agents

  摘要：

  A series of substituted phenethyl derivatives of 3-benzisothiazolylpiperazine incorporating potent D-2 and 5-HT2A antagonist activity was investigated as an approach to a novel atypical antipsychotic agent. The in vitro profile of 8e from this series is a combination of D-2 receptor affinity comparable to the typical antipsychotic agent haloperidol and a 5-HT2A/D-2 ratio comparable to the atypical agent clozapine. In vivo 8e possesses activity consistent with an efficacious antipsychotic agent with less tendency to induce extrapyramidal side effects in man.

  DOI：

  10.1021/jm950625l
• 作为产物：
  描述：

  N-乙酰基-2-羟基吲哚 在 sodium hydroxide 、 三氯化铝 、 sodium hydride 作用下， 以 甲醇 、 二硫化碳 为溶剂， 反应 0.83h， 生成 5-(2-chloroacetyl)spiro[1H-indole-3,1'-cyclopentane]-2-one
  参考文献：
  名称：

  3-Benzisothiazolylpiperazine Derivatives as Potential Atypical Antipsychotic Agents

  摘要：

  A series of substituted phenethyl derivatives of 3-benzisothiazolylpiperazine incorporating potent D-2 and 5-HT2A antagonist activity was investigated as an approach to a novel atypical antipsychotic agent. The in vitro profile of 8e from this series is a combination of D-2 receptor affinity comparable to the typical antipsychotic agent haloperidol and a 5-HT2A/D-2 ratio comparable to the atypical agent clozapine. In vivo 8e possesses activity consistent with an efficacious antipsychotic agent with less tendency to induce extrapyramidal side effects in man.

  DOI：

  10.1021/jm950625l

文献信息

• Piperazinyl-heterocyclic compounds
  申请人：PFIZER INC.

  公开号：EP0281309B1

  公开（公告）日：1991-12-27
• LOWE, JOHN A. (III);NAGEL, ARTHUR A.
  作者：LOWE, JOHN A. (III)、NAGEL, ARTHUR A.

  DOI：——

  日期：——
• US4831031A
  申请人：——

  公开号：US4831031A

  公开（公告）日：1989-05-16
• US4883795A
  申请人：——

  公开号：US4883795A

  公开（公告）日：1989-11-28
• 3-Benzisothiazolylpiperazine Derivatives as Potential Atypical Antipsychotic Agents
  作者：Harry R. Howard、John A. Lowe、Thomas F. Seeger、Patricia A. Seymour、Stevin H. Zorn、Patrick R. Maloney、Frank E. Ewing、Michael E. Newman、Anne W. Schmidt、Jerome S. Furman、Gwendolyn L. Robinson、Elisa Jackson、Celeste Johnson、Jean Morrone

  DOI：10.1021/jm950625l

  日期：1996.1.1

  A series of substituted phenethyl derivatives of 3-benzisothiazolylpiperazine incorporating potent D-2 and 5-HT2A antagonist activity was investigated as an approach to a novel atypical antipsychotic agent. The in vitro profile of 8e from this series is a combination of D-2 receptor affinity comparable to the typical antipsychotic agent haloperidol and a 5-HT2A/D-2 ratio comparable to the atypical agent clozapine. In vivo 8e possesses activity consistent with an efficacious antipsychotic agent with less tendency to induce extrapyramidal side effects in man.