1-(β-Phenylethyl)-4-(4-pyridylamino)-piperidin | 69492-63-3

• 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-(β-Phenylethyl)-4-(4-pyridylamino)-piperidin
• 英文别名: (1-phenethyl-piperidin-4-yl)-pyridin-4-yl-amine；N-[1-(2-phenylethyl)piperidin-4-yl]pyridin-4-amine
• CAS: 69492-63-3
• 化学式: C₁₈H₂₃N₃
• 分子量: 281.401
• InChiKey: AVUWCZXOAJFGBN-UHFFFAOYSA-N

物化性质

• 沸点：
  442.4±40.0 °C(Predicted)
• 密度：
  1.108±0.06 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：
  0.39
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 1-(β-Phenylethyl)-4-(4-pyridylamino)-piperidin 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以74%的产率得到OHM 3296
  参考文献：
  名称：

  New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties

  摘要：

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.

  DOI：

  10.1021/jm00123a028
• 作为产物：
  描述：

  (1-Phenethyl-piperidin-4-ylidene)-pyridin-4-yl-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 1-(β-Phenylethyl)-4-(4-pyridylamino)-piperidin
  参考文献：
  名称：

  New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties

  摘要：

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.

  DOI：

  10.1021/jm00123a028

文献信息

• Hyperpolarization of Pyridyl Fentalogues by Signal Amplification By Reversible Exchange (SABRE)
  作者：Thomas B. R. Robertson、Lysbeth H. Antonides、Nicolas Gilbert、Sophie L. Benjamin、Stuart K. Langley、Lindsey J. Munro、Oliver B. Sutcliffe、Ryan E. Mewis

  DOI：10.1002/open.201900273

  日期：2019.12

  laboratories produce analogues of fentanyl, known as fentalogues to circumvent legislation regarding its production. Three pyridyl fentalogues were synthesized and then hyperpolarized by signal amplification by reversible exchange (SABRE) to appraise the forensic potential of the technique. A maximum enhancement of ‐168‐fold at 1.4 T was recorded for the ortho pyridyl 1H nuclei. Studies of the activation parameters

  芬太尼，也被称为“困境”，是一种合成的阿片类药物，效力比吗啡高50-100倍。秘密实验室生产芬太尼的类似物，被称为fentalogues，以绕开有关其生产的立法。合成了三个吡啶基苯甲酸酯类化合物，然后通过可逆交换（SABRE）进行信号放大来超极化，以评估该技术的法医潜力。对于正吡啶基1 H核，在1.4 T时记录到最大168倍的增强。对于三个fentalogues激活参数的研究表明，配位体损失的比率反向氢化物和氢化物损失的配合物[Ir（IMES）（L）3（H）2 ] +（IMES = 1,3-双（2,4,6-三甲基苯基）咪唑-2-亚基）的范围为0.52至1.83。在地球磁场下进行SABRE之后，具有最接近于单位的比率的fentalogue产生了最大的增强作用。可以从主要由海洛因组成的基质（97：3海洛因：fentalogue）中选择性地使吡啶基苯妥英钠超极化，以验证SABER作为法医工具的用途。
• BAGLEY, JEROME R.;WYNN, RICHARD L.;RUDO, FRIEDA G.;DOORLEY, BRIAN M.;SPEN+, J. MED. CHEM., 32,(1989) N, C. 663-671
  作者：BAGLEY, JEROME R.、WYNN, RICHARD L.、RUDO, FRIEDA G.、DOORLEY, BRIAN M.、SPEN+

  DOI：——

  日期：——