3,3-dimethyl-5-(2-chloroethyl)-2,3-dihydroindol-2-one | 133833-58-6

• 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: 3,3-dimethyl-5-(2-chloroethyl)-2,3-dihydroindol-2-one
• 英文别名: 5-(2-chloroethyl)-3,3-dimethyl-1,3-dihydroindol-2-one；5-(2-chloroethyl)-3,3-dimethyl-1H-indol-2-one
• CAS: 133833-58-6
• 化学式: C₁₂H₁₄ClNO
• 分子量: 223.702
• InChiKey: GIQSEEUCXOOACD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-萘基)对二氮已环 、 3,3-dimethyl-5-(2-chloroethyl)-2,3-dihydroindol-2-one 在 sodium carbonate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 120.0h， 生成 3,3-dimethyl-5-{2-[4-(1-naphthyl)piperazinyl]ethyl}-2,3-dihydroindol-2-one
  参考文献：
  名称：

  1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents

  摘要：

  The design and synthesis of a series of potential atypical antipsychotic agents based on the structure of 1-naphthylpiperazine are described. The incorporation of dopamine antagonist activity into the parent structure was achieved with heterocyclic surrogates for the catechol moiety of dopamine. Compound 4b from this series showed a biochemical profile that translated to behavioral activity in the rat predictive of an antipsychotic agent with a low propensity to cause extrapyramidal side effects in man.

  DOI：

  10.1021/jm00110a016
• 作为产物：
  描述：

  1,2-二氢-3,3-二甲基-2-氧代-3H-吲哚 在 三乙基硅烷 、 三氯化铝 、 三氟乙酸 作用下， 以 二硫化碳 为溶剂， 生成 3,3-dimethyl-5-(2-chloroethyl)-2,3-dihydroindol-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

• [EN] N-SUBSTITUTED PIPERIDINE AND PIPERAZINE DERIVATIVES<br/>[FR] DERIVES DE PIPERIDINE ET DE PIPERAZINE N-SUBSTITUES
  申请人：WARNER LAMBERT CO

  公开号：WO2005066165A1

  公开（公告）日：2005-07-21

  This invention relates to compounds of the formula 1 wherein R1, R2, R7, R8, R9, U, V, Z, A, W, X, M, E, L, T and D are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

  这项发明涉及式1的化合物，其中R1、R2、R7、R8、R9、U、V、Z、A、W、X、M、E、L、T和D的定义如规范中所述，包含它们的药物组合物以及它们在治疗中枢神经系统和其他疾病中的用途。
• N-SUBSTITUTED PIPERIDINE AND PIPERAZINE DERIVATIVES
  申请人：Warner-Lambert Company LLC

  公开号：EP1701954A1

  公开（公告）日：2006-09-20
• 1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents
  作者：John A. Lowe、Thomas F. Seeger、Arthur A. Nagel、Harry R. Howard、Patricia A. Seymour、James H. Heym、Frank E. Ewing、Michael E. Newman、Anne W. Schmidt

  DOI：10.1021/jm00110a016

  日期：1991.6

  The design and synthesis of a series of potential atypical antipsychotic agents based on the structure of 1-naphthylpiperazine are described. The incorporation of dopamine antagonist activity into the parent structure was achieved with heterocyclic surrogates for the catechol moiety of dopamine. Compound 4b from this series showed a biochemical profile that translated to behavioral activity in the rat predictive of an antipsychotic agent with a low propensity to cause extrapyramidal side effects in man.
• 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.