{3-[(1-Phenethyl-piperidin-4-yl)-propionyl-amino]-propyl}-carbamic acid benzyl ester | 439099-18-0

• 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: {3-[(1-Phenethyl-piperidin-4-yl)-propionyl-amino]-propyl}-carbamic acid benzyl ester
• CAS: 439099-18-0
• 化学式: C₂₇H₃₇N₃O₃
• 分子量: 451.609
• InChiKey: MDOPMMRACORUGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.88
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {3-[(1-Phenethyl-piperidin-4-yl)-propionyl-amino]-propyl}-carbamic acid benzyl ester 在 palladium on activated charcoal TEA 、 氢气 、 mercury dichloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 35.0h， 生成 N-(3-Guanidino-propyl)-N-(1-phenethyl-piperidin-4-yl)-propionamide; compound with trifluoro-acetic acid
  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
• 作为产物：
  描述：

  N-(3-氨基丙基)氨基甲酸苄酯 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 {3-[(1-Phenethyl-piperidin-4-yl)-propionyl-amino]-propyl}-carbamic acid benzyl ester
  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