N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde | 159732-16-8

• 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)-1H-indol-1-amine-3-carboxaldehyde
• 英文别名: N-(n-propyl)-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde；1-(Propyl-pyridin-4-yl-amino)-1H-indole-3-carbaldehyde；1-[propyl(pyridin-4-yl)amino]indole-3-carbaldehyde
• CAS: 159732-16-8
• 化学式: C₁₇H₁₇N₃O
• 分子量: 279.341
• InChiKey: OCTRGLRMRCYOEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde 在 吡啶 、 盐酸羟胺 作用下， 反应 1.0h， 以98%的产率得到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：

  N-(吡啶-4-基)-1H-吲哚-1-胺 在 sodium hydride 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde
  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

• Use of unsubstituted and substituted n-(pyrrol-1-yl)pyridinamines as
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05776955A1

  公开（公告）日：1998-07-07

  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 the formula ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, m and n are as defined within.

  这项发明涉及一种治疗需要缓解抽搐症状的患者的方法，包括向该患者施用化合物的缓解抽搐量，该化合物的化学式为##STR1##其中R、R.sup.1、R.sup.2、R.sup.3、R.sup.4、m和n的定义如内所述。
• N-(pyridinyl)-1H-indol-1-amines
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04970218A1

  公开（公告）日：1990-11-13

  There are disclosed compounds of the formula, ##STR1## where m, n, p, R, R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification; which compounds are useful for enhancing memory and also as analgesic and antidepressant agents.

  公式中披露了化合物，其中m、n、p、R、R.sub.1、R.sub.2和R.sub.3如规范中定义；这些化合物对增强记忆、作为镇痛剂和抗抑郁剂都很有用。
• [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