贝西吡啶 | 119257-34-0

• 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
• 中文名称: 贝西吡啶
• 中文别名: 化合物 T26778
• 英文名称: N-propyl-N-(4-pyridinyl)-1H-indol-1-amine
• 英文别名: Besipirdine；N-propy-N-(4-pyridinyl)-1H-indol-1-amine；N-propyl-N-(pyridin-4-yl)-N-1H-indolyl-1-amine；N-(n-propyl)-N-(4-pyridinyl)-1H-indol-1-amine；N-propyl-N-pyridin-4-ylindol-1-amine
• CAS: 119257-34-0
• 化学式: C₁₆H₁₇N₃
• 分子量: 251.331
• InChiKey: OTPPJICEBWOCKD-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±37.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  贝西吡啶 在 吡啶 、 盐酸羟胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde oxime
  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：

  1H-吲哚-1-胺 在 sodium hydride 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 生成 贝西吡啶
  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

• Piperazine-piperidine antagonists and agonists of the 5-HT1A receptor
  申请人：Asselin Magda

  公开号：US20070027160A1

  公开（公告）日：2007-02-01

  The present invention relates to novel piperazine-piperidine compounds. The compounds are useful as 5-HT 1A binding agents, particularly as 5-HT 1A receptor antagonists and agonists. These compounds are useful in treating central nervous system disorders, such as cognition disorders, anxiety disorders, depression and sexual dysfunction.

  本发明涉及新型哌嗪-哌啶化合物。这些化合物可用作5-HT1A结合剂，特别是作为5-HT1A受体拮抗剂和激动剂。这些化合物在治疗中枢神经系统疾病方面很有用，如认知障碍、焦虑症、抑郁症和性功能障碍。
• ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR INHIBITORS
  申请人：Ghiron Chiara

  公开号：US20100016343A1

  公开（公告）日：2010-01-21

  The present invention provides compounds and compositions, methods of making them, and methods of using them to modulate α7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.

  本发明提供了化合物和组合物，制备它们的方法，以及利用它们调节α7烟碱乙酰胆碱受体和/或治疗各种疾病、疾病和症状的方法。提供的化合物可以影响神经系统、精神病和/或炎症系统等方面。
• [EN] ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR INHIBITORS<br/>[FR] INHIBITEURS DE RÉCEPTEURS NICOTINIQUES ALPHA-7 DE L'ACÉTYLCHOLINE
  申请人：WYETH CORP

  公开号：WO2010009290A1

  公开（公告）日：2010-01-21

  The present invention provides compounds and compositions, methods of making them, and methods of using them to modulate α7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory systems.

  本发明提供了化合物和组合物，制备它们的方法，以及利用它们调节α7烟碱乙酰胆碱受体和/或治疗各种疾病、疾病和症状的方法。所提供的化合物可以影响神经系统、精神病学和/或炎症系统等方面。
• [EN] PRODRUG COMPOSITIONS AND METHODS OF TREATMENT<br/>[FR] COMPOSITIONS DE PROMÉDICAMENT ET PROCÉDÉS DE TRAITEMENT
  申请人：AQUESTIVE THERAPEUTICS INC

  公开号：WO2021087359A1

  公开（公告）日：2021-05-06

  Pharmaceutical compositions include a prodrug of epinephrine are described.

  药物组合物包括表述的肾上腺素前药。
• Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients
  申请人：Rogers D. Robin

  公开号：US20070093462A1

  公开（公告）日：2007-04-26

  Disclosed are ionic liquids and methods of preparing ionic liquid compositions of active pharmaceutical, biological, nutritional, and energetic ingredients. Also disclosed are methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture.

  揭示了离子液体及制备活性药物、生物、营养和能量成分的离子液体组合物的方法。还揭示了利用本文描述的组合物的方法，以克服多型性、克服溶解度和输送问题、控制释放速率、增加功能性、增强功效（协同作用）以及改善易用性和制造工艺。