N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde oxime | 173677-77-5

• 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 oxime
• 英文别名: N-[[1-[propyl(pyridin-4-yl)amino]indol-3-yl]methylidene]hydroxylamine
• CAS: 173677-77-5
• 化学式: C₁₇H₁₈N₄O
• 分子量: 294.356
• InChiKey: DVDDLLNKDSFWDX-UHFFFAOYSA-N

物化性质

• 沸点：
  480.3±43.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 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：
  53.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-propyl-N-(4-pyridinyl)-1H-indol-1-amine-3-carboxaldehyde oxime 在 aluminum nickel sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-Aminomethyl-N-propyl-N-(4-pyridinyl)-1H-indol-1-amine dihydrochloride
  参考文献：
  名称：

  N-(pyridinyl)-1H-indol-1-amines

  摘要：

  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。

  公开号：

  US04970218A1
• 作为产物：
  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

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。
• 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
• Synthesis and Structure−Activity Relationships of <i>N</i>-Propyl-<i>N</i>-(4-pyridinyl)-1<i>H</i>-indol-1-amine (Besipirdine) and Related Analogs as Potential Therapeutic Agents for Alzheimer's Disease
  作者：Joseph T. Klein、Larry Davis、Gordon E. Olsen、George S. Wong、Francis P. Huger、Craig P. Smith、Wayne W. Petko、Michael Cornfeldt、Jeffrey C. Wilker、R. D. Blitzer、E. Landau、V. Haroutunian、Lawrence L. Martin、Richard C. Effland

  DOI：10.1021/jm9506433

  日期：1996.1.1

  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.