1-benzyl-3-(phenylamino)piperidine-3-carbonitrile | 88258-82-6

• 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: 1-benzyl-3-(phenylamino)piperidine-3-carbonitrile
• 英文别名: 1-benzyl-3-cyano-3-(N-phenylamino)piperidine；3-Anilino-1-benzylpiperidine-3-carbonitrile
• CAS: 88258-82-6
• 化学式: C₁₉H₂₁N₃
• 分子量: 291.396
• InChiKey: UUMGHRSFNJINED-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C(Solv: benzene (71-43-2))
• 沸点：
  471.5±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(phenylamino)piperidine-3-carbonitrile 在 氨 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、243.2 kPa 条件下， 反应 18.0h， 生成 tert-butyl 1-(1-benzyl-3-(phenylamino)piperidin-3-yl)-10,10-dimethyl-3,8-dioxo-9-oxa-2,5,7-triazaundecan-6-ylidenecarbamate
  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
• 作为产物：
  描述：

  氰化钾 、 1-苄基-3-哌啶酮盐酸盐 、 苯胺 以 水 、 溶剂黄146 为溶剂， 以54%的产率得到1-benzyl-3-(phenylamino)piperidine-3-carbonitrile
  参考文献：
  名称：

  Ozdowska, Zofia, Polish Journal of Chemistry, 1982, vol. 56, # 4-6, p. 811 - 813

  摘要：

  DOI：

文献信息

• OZDOWSKA, Z., POL. J. CHEM., 1982, 56, N 4-6, 811-813
  作者：OZDOWSKA, Z.

  DOI：——

  日期：——
• Nonpeptide Small Molecule Agonist and Antagonist Original Leads for Neuropeptide FF1 and FF2 Receptors
  作者：V. Blair Journigan、Christophe Mésangeau、Neha Vyas、Shainnel O. Eans、Stephen J. Cutler、Jay P. McLaughlin、Catherine Mollereau、Christopher R. McCurdy

  DOI：10.1021/jm500989n

  日期：2014.11.13

  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.
• Ozdowska, Zofia, Polish Journal of Chemistry, 1982, vol. 56, # 4-6, p. 811 - 813
  作者：Ozdowska, Zofia

  DOI：——

  日期：——