1-[2-(4-methylphenyl)ethyl]piperidin-4-amine | 893754-41-1

• 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: 1-[2-(4-methylphenyl)ethyl]piperidin-4-amine
• 英文别名: 1-(4-methylphenethyl)piperidin-4-amine
• CAS: 893754-41-1
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: DEUWCCOVOBLJCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-(4-methylphenyl)ethyl]piperidin-4-amine 、 6,9-二氯-2-甲氧基吖啶 在 sodium hydroxide 作用下， 以 苯酚 为溶剂， 反应 4.0h， 生成 6-chloro-2-methoxy-N-(1-(4-methylphenethyl)piperidin-4-yl)acridin-9-amine
  参考文献：
  名称：

  在9-氨基位置带有碱性苯基残基的功能化奎纳克林类似物的抗-病毒活性和类药物潜力

  摘要：

  在本文中，我们报道了用4-（4-甲基哌嗪-1-基）苯基，（1-苄基哌啶-4- yl）及其结构变体。发现在不同different病毒感染的鼠细胞模型的效价和活性方面，一些有前途的类似物在抗病毒方面比奎纳克林更有利。它们还表现出对人类病毒蛋白片段的更高结合亲和力（hPrP 121–231）比奎纳克林高，并且在PAMPA-BBB分析中的渗透率在CNS渗透候选物范围内。当在过表达Pgp的细胞系上进行双向分析评估时，与奎纳克林相比，一种类似物对Pgp外排活性的敏感性较低。两者合计，结果表明连接到a啶，四氢ac啶和喹啉骨架上的取代9-氨基侧链的重要作用。该侧链的性质影响基于细胞的效能，PAMPA渗透性和对hPrP 121-231的结合亲和力。

  DOI：

  10.1016/j.ejmech.2011.04.016
• 作为产物：
  描述：

  2-(4-甲基苯基)乙醇 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 39.0h， 生成 1-[2-(4-methylphenyl)ethyl]piperidin-4-amine
  参考文献：
  名称：

  Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors

  摘要：

  The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases I and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of D-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SKI. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.

  DOI：

  10.1021/jm401399c

文献信息

• [EN] SELECTIVE INHIBITORS AND ALLOSTERIC ACTIVATORS OF SPHINGOSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS ET ACTIVATEURS ALLOSTÉRIQUES DE LA SPHINGOSINE KINASE
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2014118556A3

  公开（公告）日：2014-09-25
• [EN] OXABICYCLOHEPTANES AND OXABICYCLOHEPTENES FOR THE TREATMENT OF DIABETES<br/>[FR] OXABICYCLOHEPTANES ET OXABICYCLOHEPTÈNES POUR LE TRAITEMENT DU DIABÈTE
  申请人：LIXTE BIOTECHNOLOGY INC

  公开号：WO2014005084A1

  公开（公告）日：2014-01-03

  A method of increasing the insulin sensitivity of a mammalian cell by contacting the cell with a protein phosphatase 2A (PP2A) inhibitor having the structure (I).
• Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors
  作者：Dong Jae Baek、Neil MacRitchie、Nahoum G. Anthony、Simon P. Mackay、Susan Pyne、Nigel J. Pyne、Robert Bittman

  DOI：10.1021/jm401399c

  日期：2013.11.27

  The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases I and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of D-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SKI. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.
• Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position
  作者：Thuy Nguyen、Yuji Sakasegawa、Katsumi Doh-ura、Mei-Lin Go

  DOI：10.1016/j.ejmech.2011.04.016

  日期：2011.7

  In this paper, we report the synthesis and cell-based anti-prion activity of quinacrine analogs derived by replacing the basic alkyl side chain of quinacrine with 4-(4-methylpiperazin-I-yl)phenyl, (1-benzylpiperidin-4-yl) and their structural variants. Several promising analogs were found that have a more favorable anti-prion profile than quinacrine in terms of potency and activity across different

  在本文中，我们报道了用4-（4-甲基哌嗪-1-基）苯基，（1-苄基哌啶-4- yl）及其结构变体。发现在不同different病毒感染的鼠细胞模型的效价和活性方面，一些有前途的类似物在抗病毒方面比奎纳克林更有利。它们还表现出对人类病毒蛋白片段的更高结合亲和力（hPrP 121–231）比奎纳克林高，并且在PAMPA-BBB分析中的渗透率在CNS渗透候选物范围内。当在过表达Pgp的细胞系上进行双向分析评估时，与奎纳克林相比，一种类似物对Pgp外排活性的敏感性较低。两者合计，结果表明连接到a啶，四氢ac啶和喹啉骨架上的取代9-氨基侧链的重要作用。该侧链的性质影响基于细胞的效能，PAMPA渗透性和对hPrP 121-231的结合亲和力。