N-((4-methylphenyl)methyl)amino-1-phenylmethylpyrrolidine | 359878-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((4-methylphenyl)methyl)amino-1-phenylmethylpyrrolidine
• 英文别名: 1-benzyl-N-(4-methylbenzyl)pyrrolidin-3-amine；1-benzyl-N-[(4-methylphenyl)methyl]pyrrolidin-3-amine
• CAS: 359878-11-8
• 化学式: C₁₉H₂₄N₂
• 分子量: 280.413
• InChiKey: KAVGFUSYIFGSSP-UHFFFAOYSA-N

物化性质

• 沸点：
  401.9±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

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：
  0.368
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((4-methylphenyl)methyl)amino-1-phenylmethylpyrrolidine 、 异氰酸苄酯 以 二氯甲烷 为溶剂， 反应 48.0h， 以92%的产率得到N-((4-methylphenyl)methyl)-N-(1-(phenylmethyl)pyrrolidin-3-yl)-N'-phenylmethylcarbamide
  参考文献：
  名称：

  AZACYCLIC COMPOUNDS

  摘要：

  提供用于治疗修改血清素能受体活性具有有益效果的疾病状态的化合物和方法。在方法中，将有效量的化合物施用于需要此类治疗的病人。

  公开号：

  US20150259291A1
• 作为产物：
  描述：

  N-(1-benzylpyrrolidin-3-yl)-1-(p-tolyl)methanimine 在 甲醇 、 sodium tetrahydroborate 作用下， 以61%的产率得到N-((4-methylphenyl)methyl)amino-1-phenylmethylpyrrolidine
  参考文献：
  名称：

  Design, synthesis, and multitargeted profiling of N-benzylpyrrolidine derivatives for the treatment of Alzheimer’s disease

  摘要：

  Multitarget molecular hybrids of N-benzyl pyrrolidine derivatives were designed, synthesized, and biologically evaluated for the treatment of Alzheimer's disease (AD). Among the synthesized compounds, 4k and 4o showed balanced enzyme inhibitions against cholinesterases (AChE and BChE) and BACE-1. Both leads showed considerable PAS-AChE binding capability, excellent brain permeation, potential disassembly of Aβ aggregates, and neuroprotective activity against Aβ-induced stress. Compounds 4k and 4o also ameliorated cognitive dysfunction against the scopolamine-induced amnesia model in the Y-maze test. The ex vivo study signified attenuated brain AChE activity and antioxidant potential of compounds 4k and 4o. Furthermore, compound 4o also showed improvement in Aβ-induced cognitive dysfunction by the Morris water maze test with excellent oral absorption characteristics ascertained by the pharmacokinetic study. In silico molecular docking and dynamics simulation studies of leads suggested their consensual binding affinity toward PAS-AChE in addition to aspartate dyad of BACE-1.

  DOI：

  10.1016/j.bmc.2020.115721

文献信息

• Catalysts and methods for enantioselective conjugate additions of amines to unsaturated electrophiles
  申请人：Northwestern University

  公开号：US10781172B2

  公开（公告）日：2020-09-22

  Disclosed are complexes and methods of using the complexes as catalysts for addition of amines to unsaturated electrophiles, as well as novel compounds produced by the disclosed complexes and methods. The disclosed methods may utilize the disclosed complexes as catalysts for adding unprotected primary amines and secondary amines to unsaturated electrophiles in an enantioselective manner to produce novel compounds which may include amino substituted succinimide compounds.

  所公开的是络合物和使用络合物作为催化剂将胺加到不饱和亲电体上的方法，以及用所公开的络合物和方法生产的新型化合物。所公开的方法可利用所公开的络合物作为催化剂，以对映选择性的方式将未保护的伯胺和仲胺添加到不饱和亲电体中，从而生产出新型化合物，其中可包括氨基取代的琥珀酰亚胺化合物。
• WO2007/124136
  申请人：——

  公开号：——

  公开（公告）日：——
• CATALYSTS AND METHODS FOR ENANTIOSELECIVE CONJUGATE ADDITION OF AMINES TO UNSATURATED ELECTROPHILES
  申请人：Northwestern University

  公开号：US20210002221A1

  公开（公告）日：2021-01-07

  Disclosed are complexes and methods of using the complexes as catalysts for addition of amines to unsaturated electrophiles, as well as novel compounds produced by the disclosed complexes and methods. The disclosed methods may utilize the disclosed complexes as catalysts for adding unprotected primary amines and secondary amines to unsaturated electrophiles in an enantioselective manner to produce novel compounds which may include amino substituted succinimide compounds.
• AZACYCLIC COMPOUNDS
  申请人：ACADIA Pharmaceuticals Inc.

  公开号：US20150259291A1

  公开（公告）日：2015-09-17

  Compounds and methods are provided for the treatment of disease conditions in which modification of serotonergic receptor activity has a beneficial effect. In the method, an effective amount of a compound is adminstered to a patient in need of such treatment.

  提供用于治疗修改血清素能受体活性具有有益效果的疾病状态的化合物和方法。在方法中，将有效量的化合物施用于需要此类治疗的病人。
• Design, synthesis, and multitargeted profiling of N-benzylpyrrolidine derivatives for the treatment of Alzheimer’s disease
  作者：Priyanka Kumari Choubey、Avanish Tripathi、Piyoosh Sharma、Sushant Kumar Shrivastava

  DOI：10.1016/j.bmc.2020.115721

  日期：2020.11

  Multitarget molecular hybrids of N-benzyl pyrrolidine derivatives were designed, synthesized, and biologically evaluated for the treatment of Alzheimer's disease (AD). Among the synthesized compounds, 4k and 4o showed balanced enzyme inhibitions against cholinesterases (AChE and BChE) and BACE-1. Both leads showed considerable PAS-AChE binding capability, excellent brain permeation, potential disassembly of Aβ aggregates, and neuroprotective activity against Aβ-induced stress. Compounds 4k and 4o also ameliorated cognitive dysfunction against the scopolamine-induced amnesia model in the Y-maze test. The ex vivo study signified attenuated brain AChE activity and antioxidant potential of compounds 4k and 4o. Furthermore, compound 4o also showed improvement in Aβ-induced cognitive dysfunction by the Morris water maze test with excellent oral absorption characteristics ascertained by the pharmacokinetic study. In silico molecular docking and dynamics simulation studies of leads suggested their consensual binding affinity toward PAS-AChE in addition to aspartate dyad of BACE-1.