2-苯并硫杂氮醇胺,N-[1-(2-苯基乙基)-4-哌啶基]- | 104588-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-苯并硫杂氮醇胺,N-[1-(2-苯基乙基)-4-哌啶基]-
• 英文名称: 1-phenethyl-4-piperidine
• 英文别名: N-[1-(2-phenylethyl)piperidin-4-yl]-1,3-benzothiazol-2-amine
• CAS: 104588-49-0
• 化学式: C₂₀H₂₃N₃S
• 分子量: 337.489
• InChiKey: XQOOGDUJNHGVJG-UHFFFAOYSA-N

物化性质

• 熔点：
  118.1 °C
• 沸点：
  485.3±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  28.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  呋喃甲酰氯 、 2-苯并硫杂氮醇胺,N-[1-(2-苯基乙基)-4-哌啶基]- 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以68%的产率得到N-(1,3-benzothiazol-2-yl)-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide
  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-苯乙基-哌啶-4-酮肟 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 异戊醇 为溶剂， 生成 2-苯并硫杂氮醇胺,N-[1-(2-苯基乙基)-4-哌啶基]-
  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

• 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：——
• STOKBROEKX, RAYMOND A.;LUYCKX, MARCEL G. M.;JANSSENS, FRANS E.
  作者：STOKBROEKX, RAYMOND A.、LUYCKX, MARCEL G. M.、JANSSENS, FRANS E.

  DOI：——

  日期：——