N-propyl-N-(4-pyridinyl)-3-ethenyl-1H-indol-1-amine | 159732-18-0

• 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: N-propyl-N-(4-pyridinyl)-3-ethenyl-1H-indol-1-amine
• 英文别名: 3-ethenyl-N-propyl-N-pyridin-4-ylindol-1-amine
• CAS: 159732-18-0
• 化学式: C₁₈H₁₉N₃
• 分子量: 277.369
• InChiKey: DQHQVPADTYDJMD-UHFFFAOYSA-N

物化性质

• 沸点：
  441.819±37.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.061±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-propyl-N-(4-pyridinyl)-3-ethenyl-1H-indol-1-amine 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-ethyl-N-propyl-N-(4-pyridinyl)-1H-indol-1-amine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine (Besipirdine) and Related Analogs as Potential Therapeutic Agents for Alzheimer's Disease

  摘要：

  A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N-(4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [H-3]quinuclidinyl benzilate binding, in. vivo reversal of scopolamine-induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [H-3]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.

  DOI：

  10.1021/jm9506433
• 作为产物：
  描述：

  N-(吡啶-4-基)-1H-吲哚-1-胺 在 potassium tert-butylate 、 sodium hydride 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 N-propyl-N-(4-pyridinyl)-3-ethenyl-1H-indol-1-amine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-Propyl-N-(4-pyridinyl)-1H-indol-1-amine (Besipirdine) and Related Analogs as Potential Therapeutic Agents for Alzheimer's Disease

  摘要：

  A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N-(4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [H-3]quinuclidinyl benzilate binding, in. vivo reversal of scopolamine-induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [H-3]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.

  DOI：

  10.1021/jm9506433

文献信息

• [EN] USE OFF UNSUBSTITUTED AND SUBSTITUTED N-(PYRROL-1-YL)PYRIDINAMINES AS ANTICONVULSANT AGENTS<br/>[FR] UTILISATION DE N-(PYRROL-1-YL)PYRIDINAMINES SUBSTITUEES ET NON SUBSTITUEES EN TANT QU'AGENTS ANTICONVULSIVANTS
  申请人：HOECHST MARION ROUSSEL, INC.

  公开号：WO1997004777A1

  公开（公告）日：1997-02-13

  (EN) This invention relates to a method of treating a patient in need of relief from convulsions which comprises administering to such a patient a convulsion-alleviating amount of a compound of formula (I), wherein R, R1, R2, R3, R4, m and n are as defined within.(FR) Procédé de traitement d'un patient souffrant de convulsions, qui consiste à administrer à ce patient une quantité suffisante pour atténuer les convulsions d'un composé de formule (I) dans laquelle R, R1, R2, R3, R4, m et n sont tels que définis dans le descriptif.

  该发明涉及一种治疗需要缓解抽搐症状的患者的方法，包括向该患者施用公式（I）化合物的缓解抽搐的剂量，其中R、R1、R2、R3、R4、m和n如描述中所定义。(翻译结果)
• USE OF UNSUBSTITUTED AND SUBSTITUTED N-(PYRROL-1-YL)PYRIDINAMINES AS ANTICONVULSANT AGENTS
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP0840609B1

  公开（公告）日：2002-06-05
• Use of N-(Pyridinyl)-1H-Indol-1-Amines for the preparation of a medicament for the treatment of obsessive-compulsive disorders
  申请人：HOECHST MARION ROUSSEL, Inc.

  公开号：EP0635269B1

  公开（公告）日：1999-11-03
• US4970218A
  申请人：——

  公开号：US4970218A

  公开（公告）日：1990-11-13
• US5039811A
  申请人：——

  公开号：US5039811A

  公开（公告）日：1991-08-13