N-(3-aminopropyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide | 439099-19-1

• 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: N-(3-aminopropyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
• CAS: 439099-19-1
• 化学式: C₁₉H₃₁N₃O
• 分子量: 317.475
• InChiKey: UXMDOEYHHJBBGD-UHFFFAOYSA-N

物化性质

• 沸点：
  469.7±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-aminopropyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide 在 三乙胺 、 三氟乙酸 、 mercury dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-(3-Guanidino-propyl)-N-(1-phenethyl-piperidin-4-yl)-propionamide
  参考文献：
  名称：

  Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for μ-opioid receptors and I2-imidazoline binding sites

  摘要：

  A new series of fentanyl derivatives [i.e., N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinoalkyl)propanamide] bearing aliphatic alkaneguanidinium moieties were prepared. Their affinities for the V opioid receptors and for the I-2-imidazoline binding sites (I-2-IBS) were determined on human post-mortem prefrontal cortex membranes. All of these hybrid compounds had significant and/or very high affinity for both receptors in the nanomolar range, meaning an improvement compared to the prototype N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinopropyl)propanamide previously reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.048
• 作为产物：
  描述：

  [3-(1-Phenethyl-piperidin-4-ylamino)-propyl]-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 N-(3-aminopropyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
  参考文献：
  名称：

  Guanidinium and aminoimidazolinium derivatives of N-(4-piperidyl)propanamides as potential ligands for μ opioid and I2-imidazoline receptors: synthesis and pharmacological screening

  摘要：

  Derivatives of N-(1-phenethyl-4-piperidyl)propanamides incorporating guanidinium and 2-aminoimidazolinium groups have been prepared by a synthetic approach involving first introduction of a spacer between the piperidine and the functional group by reductive amination of piperidinone. The formation of each of these functional groups was carried out using N-N'-di(tert-butoxycarbonyl)thiourca and 2-methylthioimidazolinium iodide, respectively. These structures have been designed to incorporate two pharmacologic goals into one entity. Radioligand binding assays have been used to study their affinity for opioid (A, 5 and K) and 1(2)-imidazoline receptors. Two of them, 10 and 16, showed high affinity for mu opioid receptors and functionally they had moderate analgesic properties in the hot plate and writhing tests. The in vitro studies on guinea pig ileum (GPI) indicated that both compounds are mu opioid agonists. In what concerns 12-imidazoline receptor activity, these derivatives showed low affinity around 6 to 7 times less than idazoxan. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00356-x

文献信息

• Guanidinium and aminoimidazolinium derivatives of N-(4-piperidyl)propanamides as potential ligands for μ opioid and I2-imidazoline receptors: synthesis and pharmacological screening
  作者：Ana Montero、Pilar Goya、Nadine Jagerovic、Luis F Callado、J.Javier Meana、Rocı́o Girón、Carlos Goicoechea、Mª Isabel Martı́n

  DOI：10.1016/s0968-0896(01)00356-x

  日期：2002.4

  Derivatives of N-(1-phenethyl-4-piperidyl)propanamides incorporating guanidinium and 2-aminoimidazolinium groups have been prepared by a synthetic approach involving first introduction of a spacer between the piperidine and the functional group by reductive amination of piperidinone. The formation of each of these functional groups was carried out using N-N'-di(tert-butoxycarbonyl)thiourca and 2-methylthioimidazolinium iodide, respectively. These structures have been designed to incorporate two pharmacologic goals into one entity. Radioligand binding assays have been used to study their affinity for opioid (A, 5 and K) and 1(2)-imidazoline receptors. Two of them, 10 and 16, showed high affinity for mu opioid receptors and functionally they had moderate analgesic properties in the hot plate and writhing tests. The in vitro studies on guinea pig ileum (GPI) indicated that both compounds are mu opioid agonists. In what concerns 12-imidazoline receptor activity, these derivatives showed low affinity around 6 to 7 times less than idazoxan. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for μ-opioid receptors and I2-imidazoline binding sites
  作者：Christophe Dardonville、Nadine Jagerovic、Luis F Callado、J.Javier Meana

  DOI：10.1016/j.bmcl.2003.10.048

  日期：2004.1

  A new series of fentanyl derivatives [i.e., N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinoalkyl)propanamide] bearing aliphatic alkaneguanidinium moieties were prepared. Their affinities for the V opioid receptors and for the I-2-imidazoline binding sites (I-2-IBS) were determined on human post-mortem prefrontal cortex membranes. All of these hybrid compounds had significant and/or very high affinity for both receptors in the nanomolar range, meaning an improvement compared to the prototype N-[1-(2-phenethyl)-4-piperidyl]-N-(guanidinopropyl)propanamide previously reported. (C) 2003 Elsevier Ltd. All rights reserved.