4-(aminomethyl)-1-benzyl-N-phenylpiperidin-4-amine | 181642-34-2

• 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: 4-(aminomethyl)-1-benzyl-N-phenylpiperidin-4-amine
• 英文别名: 4-(Aminomethyl)-1,4-dibenzylpiperidine；(1,4-Dibenzylpiperidin-4-yl)methanamine
• CAS: 181642-34-2
• 化学式: C₂₀H₂₆N₂
• 分子量: 294.44
• InChiKey: SAFFDSTYKHSMJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-(aminomethyl)-1-benzyl-N-phenylpiperidin-4-amine 、 环丙基甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到
  参考文献：
  名称：

  The design and discovery of novel amide CCR5 antagonists

  摘要：

  The synthesis of a range of novel amine-containing structures and their primary potency as inhibitors of HIV-1 fusion via blocking of the CCR5 receptor is described. The development of the medicinal chemistry strategy and SAR's which led to the identification of the piperidine amide compounds 33 and 36 as excellent leads for further evaluation is described, along with key physicochemical data which highlighted their lead potential. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.012
• 作为产物：
  描述：

  1-苄基-4-氰基哌啶 在 氨 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 乙基苯 为溶剂， -70.0~20.0 ℃ 、273.6 kPa 条件下， 反应 2.5h， 生成 4-(aminomethyl)-1-benzyl-N-phenylpiperidin-4-amine
  参考文献：
  名称：

  Nonpeptide Small Molecule Agonist and Antagonist Original Leads for Neuropeptide FF1 and FF2 Receptors

  摘要：

  Neuropeptide FF1 and FF2 receptors (NPFF1-R and NPFF2-R), and their endogenous ligand NPFF, are one of only several systems responsible for mediating opioid-induced hyperalgesia, tolerance, and dependence. Currently, no small molecules displaying good affinity or selectivity for either subtype have been reported, to decipher the role of NPFF2-R as it relates to opioid-mediated analgesia, for further exploration of NPFF1-R, or for medication development for either subtype. We report the first nonpeptide small molecule scaffold for NPFF1,2-R, the guanidino-piperidines, and SAR studies resulting in the discovery of a NPFF1 agonist (7b, K-i = 487 +/- 117 nM), a NPFF1 antagonist (46, K-i = 81 +/- 17 nM), and a NPFF2 partial antagonist (53a, K-i = 30 +/- 5 nM), which serve as leads for the development of pharmacological probes and potential therapeutic agents. Testing of 46 alone was without effect in the mouse 48 degrees C warm-water tail-withdrawal test, but pretreatment with 46 prevented NPFF-induced hyperalgesia.

  DOI：

  10.1021/jm500989n

文献信息

• [EN] SUBSTITUTED HETEROCYCLIC COMPOUNDS, PREPARATION METHOD THEREFOR AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] COMPOSES HETEROCYCLIQUES SUBSTITUES, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SANOFI

  公开号：WO1996023787A1

  公开（公告）日：1996-08-08

  (EN) Compounds of formula (I), wherein A is a bivalent radical selected from: A1)-O-CO-, A2)-CH2-O-CO-, A3)-O-CH2-CO-, A4)-O-CH2-CH2-, A5-N(R1)-CO-, A6)-N(R1)-CO-CO-, A7)-N(R1)-CH2-CH2-, A8)-O-CH2-, where R1 is hydrogen or C1-4alkyl, and Am is a heterocyclic nitrogen ring, are provided for use as neurokinin receptor antagonists.(FR) L'invention a pour objet des composés de formula (I) dans laquelle A représente un radical bivalent choisi parmi: A1)-O-CO-, A2)-CH2-O-CO-, A3)-O-CH2-CO-, A4)-O-CH2-CH2-, A5-N(R1)-CO-, A6)-N(R1)-CO-CO-, A7)-N(R1)-CH2-CH2-, A8)-O-CH2-, dans lesquels R1 représente un hydrogène ou un (C1-C4)alkyle, Am représente un hétérocyclique azoté. Application: antagonistes des récepteurs des neurokinines.

  化合物的式子为（I），其中A是双价基团，选择自：A1）-O-CO-，A2）-CH2-O-CO-，A3）-O-CH2-CO-，A4）-O-CH2-CH2-，A5-N（R1）-CO-，A6）-N（R1）-CO-CO-，A7）-N（R1）-CH2-CH2-，A8）-O-CH2-，其中R1表示氢或C1-4烷基，而Am是一个杂环氮环，用作神经激肽受体拮抗剂。
• HETEROCYCLO INHIBITORS OF POTASSIUM CHANNEL FUNCTION
  申请人：Lloyd John

  公开号：US20090312307A1

  公开（公告）日：2009-12-17

  Novel heterocyclo compounds useful as inhibitors of potassium channel function (especially inhibitors of the K v 1 subfamily of voltage gated K + channels, especially inhibitors K v 1.5 which has been linked to the ultra-rapidly activating delayed rectifier K + current I Kur ), methods of using such compounds in the prevention and treatment of arrhythmia and I Kur -associated conditions, and pharmaceutical compositions containing such compounds.

  新型杂环化合物，可作为钾通道功能抑制剂使用（特别是Kv1亚家族电压门控K+通道的抑制剂，特别是与超快速激活延迟整流K+电流IKur相关的Kv1.5抑制剂），使用这种化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这种化合物的制药组合物。
• Heterocyclo inhibitors of potassium channel function
  申请人：Bristol-Myers Squibb Company

  公开号：EP2228065A2

  公开（公告）日：2010-09-15

  Novel heterocyclo compounds of formulae (i), (ii) and (iii) useful as inhibitors of potassium channel function (especially inhibitors of the Kv1 subfamily of voltage gated K+ channels, especially inhibitors Kv1.5 which has been linked to the ultra-rapidly activating delayed rectifier K+ current IKur), methods of using such compounds in the prevention and treatment of arrhythmia and IKur-associated conditions, and pharmaceutical compositions containing such compounds.

  式(i)、(ii)和(iii)的新型杂环化合物，可用作钾通道功能抑制剂（特别是电压门控K+通道Kv1亚族的抑制剂，尤其是与超快速活化延迟整流K+电流IKur有关的Kv1.5抑制剂），使用此类化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有此类化合物的药物组合物。
• COMPOSES HETEROCYCLIQUES SUBSTITUES, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SANOFI-SYNTHELABO

  公开号：EP0807111B1

  公开（公告）日：2002-08-14
• Composés hétérocycliques substitués, procédé pour leur préparation et compositions pharmaceutiques les contenant
  申请人：Sanofi-Aventis

  公开号：EP1156049B1

  公开（公告）日：2005-06-01