1-benzyl-N-(4-(trifluoromethyl)benzyl)piperidin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-N-(4-(trifluoromethyl)benzyl)piperidin-4-amine
• 英文别名: 1-benzyl-N-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-amine
• 化学式: C₂₀H₂₃F₃N₂
• mdl: MFCD20257746
• 分子量: 348.411
• InChiKey: KAYKWKOWEOGULE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl-N-(4-(trifluoromethyl)benzyl)piperidin-4-amine 在 硝基甲烷 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 作用下， 以 乙腈 为溶剂， 生成 N-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-amine
  参考文献：
  名称：

  光氧化还原催化促进叔胺的温和且官能团耐受的有氧 N-脱烷基化

  摘要：

  本文介绍了一种通过光氧化还原催化叔胺N-脱烷基化的温和方法的开发及其在后期功能化中的应用。使用所开发的方法，超过 30 种不同的脂肪族、苯胺型和复杂底物被证明可以进行N-脱烷基化，与文献中的方法相比，提供了一种具有更广泛官能团耐受性的方法。该范围还包括具有复杂子结构和药物底物的叔胺和仲胺分子。有趣的是，在几个环状子结构中观察到亚胺的α-氧化而不是N-脱烷基化，这表明亚胺是相关的反应中间体。

  DOI：

  10.1021/acs.joc.3c00656
• 作为产物：
  描述：

  N-(1-benzylpiperidin-4-yl)-1-(4-(trifluoromethyl)phenyl)methanimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以82%的产率得到1-benzyl-N-(4-(trifluoromethyl)benzyl)piperidin-4-amine
  参考文献：
  名称：

  Design and development of multitarget-directed N-Benzylpiperidine analogs as potential candidates for the treatment of Alzheimer's disease

  摘要：

  The multitarget-directed strategy offers an effective and promising paradigm to treat the complex neurodegenerative disorder, such as Alzheimer's disease (AD). Herein, a series of N-benzylpiperidine analogs (17-31 and 32-46) were designed and synthesized as multi-functional inhibitors of acetyl cholinesterase (AChE) and beta-secretase-1 (BACE-1) with moderate to excellent inhibitory activities. Among the tested inhibitors, 25, 26, 40, and 41 presented the most significant and balanced inhibition against both the targets. Compounds 40 and 41 exhibited high brain permeability in the PAMPA-BBB assay, significant displacement of propidium iodide from the peripheral anionic site (PAS) of AChE, and were devoid of neurotoxicity towards SH-SY5Y neuroblastoma cell lines up to the maximum tested concentration of 80 mu M. Meanwhile, both these compounds inhibited self- and AChE-induced A beta aggregation in thioflavin T assay, which was also re-affirmed by morphological characterization of All aggregates using atomic force microscopy (AFM). Moreover, 40 and 41 ameliorated the scopolamine induced cognitive impairment in elevated plus and Y-maze experiments. Ex vivo and biochemical analysis established the brain AChE inhibitory potential and antioxidant properties of these compounds. Further, improvement in A beta(1-42)-induced cognitive impairment was also observed by compound 41 in the Morris water maze experiment with significant oral absorption characteristics ascertained by the pharmacokinetic studies. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.030

文献信息

• SUBSTITUTED AMINO-AZA-CYCLOALKANES USEFUL AGAINST MALARIA
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1322612A1

  公开（公告）日：2003-07-02
• [EN] SUBSTITUTED AMINO-AZA-CYCLOALKANES USEFUL AGAINST MALARIA<br/>[FR] AMINO-AZA-CYCLOALCANES SUBSTITUES UTILES CONTRE LA MALARIA
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2002024649A1

  公开（公告）日：2002-03-28

  The invention relates to novel compounds which are substituted amino-aza-cycloalkane derivatives of the general formula I. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more compounds of general formula I and especially their use as inhibitors of the plasmodium falciparum protease plasmepsin II or related aspartic proteases.