1-((2S)-2-vinylindolinyl)-2-{4-[(4-methylphenyl)methyl]piperazinyl}ethan-1-one | 313235-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-((2S)-2-vinylindolinyl)-2-{4-[(4-methylphenyl)methyl]piperazinyl}ethan-1-one
• 英文别名: 1-[(2S)-2-ethenyl-2,3-dihydroindol-1-yl]-2-[4-[(4-methylphenyl)methyl]piperazin-1-yl]ethanone
• CAS: 313235-07-3
• 化学式: C₂₄H₂₉N₃O
• 分子量: 375.514
• InChiKey: AOGRGGFEDGZZJY-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((2S)-2-vinylindolinyl)-2-{4-[(4-methylphenyl)methyl]piperazinyl}ethan-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 生成 1-((R)-2-Ethyl-2,3-dihydro-indol-1-yl)-2-[4-(4-methyl-benzyl)-piperazin-1-yl]-ethanone
  参考文献：
  名称：

  Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 2: Asymmetric synthesis and biological evaluation

  摘要：

  A series of chiral benzylpiperazinyl-1-(2,3-dihydro-indol-1-yl)ethanone derivatives were prepared and examined for their affinity at dopamine D-2 and D-4 receptors. Three compounds having D-2/D-4 affinity ratios approximating that found for the atypical neuroleptic clozapine were further evaluated in behavioral tests of antipsychotic efficacy and motor side effects. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00656-x
• 作为产物：
  描述：

  (S)-2-vinylindoline 在 TEA 、 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 3.0h， 生成 1-((2S)-2-vinylindolinyl)-2-{4-[(4-methylphenyl)methyl]piperazinyl}ethan-1-one
  参考文献：
  名称：

  Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 2: Asymmetric synthesis and biological evaluation

  摘要：

  A series of chiral benzylpiperazinyl-1-(2,3-dihydro-indol-1-yl)ethanone derivatives were prepared and examined for their affinity at dopamine D-2 and D-4 receptors. Three compounds having D-2/D-4 affinity ratios approximating that found for the atypical neuroleptic clozapine were further evaluated in behavioral tests of antipsychotic efficacy and motor side effects. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00656-x

文献信息

• Benzylpiperazinyl-indolinylethanones
  申请人：Neurogen Corporation.

  公开号：US20020128274A1

  公开（公告）日：2002-09-12

  Disclosed are benzylpiperazinyl-indolinylethanone compounds which are useful for the treatment and/or prevention of neuropsychological disorders including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents. Pharmaceutical compositions, including packaged pharmaceutical compositions, are further provided. Compounds of the invention are also useful as probes for the localization of GABA A receptors in tissue samples.

  揭示了苯甲基哌嗪基吲哚基乙酮类化合物，其可用于治疗和/或预防神经心理障碍，包括但不限于精神分裂症、狂躁症、痴呆、抑郁症、焦虑症、强迫行为、物质滥用、帕金森病样运动障碍和与神经阻滞剂使用相关的运动障碍。此外，还提供了制药组合物，包括包装的制药组合物。该发明的化合物还可用作组织样本中GABAA受体的定位探针。
• US6355644B1
  申请人：——

  公开号：US6355644B1

  公开（公告）日：2002-03-12
• [EN] BENZYLPIPERAZINYL-INDOLINYLETHANONES<br/>[FR] BENZYLPIPERAZINYL-INDOLINYLETHANONES
  申请人：NEUROGEN CORP

  公开号：WO2000076967A1

  公开（公告）日：2000-12-21

  Disclosed are benzylpiperazinyl-indolinylethanone compounds which are useful for the treatment and/or prevention of neuropsychological disorders, including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents. Pharmaceutical compositions, including packaged pharmaceutical compositions, are further provided. Compounds of the invention are also useful as probes for the localization of GABAA receptors in tissue samples.
• Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 2: Asymmetric synthesis and biological evaluation
  作者：He Zhao、Xiaoshu He、Andrew Thurkauf、Diane Hoffman、Andrzej Kieltyka、Robbin Brodbeck、Renee Primus、Jan W.F Wasley

  DOI：10.1016/s0960-894x(02)00656-x

  日期：2002.11

  A series of chiral benzylpiperazinyl-1-(2,3-dihydro-indol-1-yl)ethanone derivatives were prepared and examined for their affinity at dopamine D-2 and D-4 receptors. Three compounds having D-2/D-4 affinity ratios approximating that found for the atypical neuroleptic clozapine were further evaluated in behavioral tests of antipsychotic efficacy and motor side effects. (C) 2002 Elsevier Science Ltd. All rights reserved.