3-(1-dimethylaminoethylidene)-1,3-dihydroindol-2-one | 91505-81-6

• 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-(1-dimethylaminoethylidene)-1,3-dihydroindol-2-one
• 英文别名: 3-(α-dimethylaminoethylidene)oxindole；3-(1-dimethylaminoethylidene)-2(1H,3H)-indolone；3-[1-(dimethylamino)ethylidene]-1H-indol-2-one
• CAS: 91505-81-6
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: KFRVPIVORKPRNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  204-207 °C
• 沸点：
  374.7±42.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-dimethylaminoethylidene)-1,3-dihydroindol-2-one 以 正己烷 为溶剂， 反应 18.0h， 生成 1-(3-Methylphenyl)-3-(1-dimethylaminoethylidene)-2(1H,3H)-indolone
  参考文献：
  名称：

  Method of treating anxiety and depression with

  摘要：

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或逆转先前或同时给予的神经阻滞剂药物的副作用方面非常有价值；或在治疗癫痫方面也非常有价值。更广泛的一类取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，以及1-苯基-3-(2-吡咯烷亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面也非常有价值。

  公开号：

  US04977178A1
• 作为产物：
  描述：

  3-Dimethylaminomethylene-2,3-dihydro-1H-indol-2-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 3-(1-dimethylaminoethylidene)-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Lactam and amide acetals. 69. Synthesis and properties of 3-(aminomethylene)-2-indolinone derivatives

  摘要：

  DOI：

  10.1007/bf00484357

文献信息

• Heteroylidene indolone compounds
  申请人：Pfizer Inc.

  公开号：US04476307A1

  公开（公告）日：1984-10-09

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或翻转先前或同时给予的神经精神药物的副作用方面非常有价值；或在治疗癫痫方面也非常有价值。一类更广泛的取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，以及1-苯基-3-(2-吡咯烷基亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面也非常有价值。
• 1-phenyl-2(1H,3H)-indolone psycho-therapeutic agents
  申请人：Pfizer Inc.

  公开号：US04861880A1

  公开（公告）日：1989-08-29

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或逆转先前或同时给予的神经类药物的副作用，或治疗癫痫方面具有价值。更广泛的一类取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，连同1-苯基-3-(2-吡咯烷基亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面具有价值。
• 1-Phenyl-2(1H,3H)-indolone psychotherapeutic agents
  申请人：Pfizer Inc.

  公开号：US04879391A1

  公开（公告）日：1989-11-07

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidiene-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或逆转先前或同时给予的神经类药物副作用方面非常有价值；或在治疗癫痫方面也有用。更广泛的取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，连同1-苯基-3-(2-吡咯烷基亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面也很有价值。
• Oxindole-Based Inhibitors of Cyclin-Dependent Kinase 2 (CDK2):  Design, Synthesis, Enzymatic Activities, and X-ray Crystallographic Analysis
  作者：H. Neal Bramson、John Corona、Stephen T. Davis、Scott H. Dickerson、Mark Edelstein、Stephen V. Frye、Robert T. Gampe、Phil A. Harris、Anne Hassell、William D. Holmes、Robert N. Hunter、Karen E. Lackey、Brett Lovejoy、Michael J. Luzzio、Val Montana、Warren J. Rocque、David Rusnak、Lisa Shewchuk、James M. Veal、Duncan H. Walker、Lee F. Kuyper

  DOI：10.1021/jm010117d

  日期：2001.12.1

  Two closely related classes of oxindole-based compounds, 1H-indole-2,3-dione 3-phenylhydrazones and 3-(anilinomethylene)-1,3-dihydro-2H-indol-2-ones, were shown to potently inhibit cyclin-dependent kinase 2 (CDK2). The initial lead compound was prepared as a homologue of the 3-benzylidene-1,3-dihydro-2H-indol-2-one class of kinase inhibitor. Crystallographic analysis of the lead compound bound to CDK2 provided the basis for analogue design. A semiautomated method of ligand docking was used to select compounds for synthesis, and a number of compounds with low nanomolar inhibitory activity versus CDK2 were identified. Enzyme binding determinants for several analogues were evaluated by X-ray crystallography. Compounds in this series inhibited CDK2 with a potency similar to 10-fold greater than that for CDK1. Members of this class of inhibitor cause an arrest of the cell cycle and have shown potential utility in the prevention of chemotherapy-induced alopecia.
• Lactam and amide acetals. 69. Synthesis and properties of 3-(aminomethylene)-2-indolinone derivatives
  作者：T. V. Golovko、N. P. Solov'eva、G. A. Bogdanova、Yu. N. Sheinker、V. G. Granik

  DOI：10.1007/bf00484357

  日期：1991.9