(R)-(-)-2-(1-(2-allylphenoxy)ethyl)-4,5-dihydro-1H-imidazole | 1253420-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-(-)-2-(1-(2-allylphenoxy)ethyl)-4,5-dihydro-1H-imidazole
• 英文别名: (R)-(-)-allyphenyline；allyphenyline；2-[(1R)-1-(2-prop-2-enylphenoxy)ethyl]-4,5-dihydro-1H-imidazole
• CAS: 1253420-66-4
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: MNMDMCKHXVHLAW-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-乳酸甲酯 、 乙二胺 、 2-烯丙基酚 在 三苯基膦 、 偶氮二甲酸二乙酯 、 三甲基铝 、 甲醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (R)-(-)-2-(1-(2-allylphenoxy)ethyl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Fruitful Adrenergic α_2C-Agonism/α_2A-Antagonism Combination to Prevent and Contrast Morphine Tolerance and Dependence^,

  摘要：

  The functional in vitro study of the enantiomers of imidazolines 4-7 highlighted the role played by the nature of the ortho phenyl substituent in determining the preferred alpha(2C)-AR configuration. Indeed, the (S) enantiomers of 4-6 or (R) enantiomer of 7 behave as eutomers and activate this subtype as full agonists; the corresponding distomers are partial agonists. Because in clinical pain management with opioids alpha(2C)-AR agonists, devoid of the alpha(2A)-AR-mediated side effects, may represent an improvement over current therapies with clonidine like drugs, 4 and its enantiomers, showing alpha(2C)-agonism/alpha(2A)-Aantagonism, have been studied in vivo. The data suggest that partial alpha(2C)-activation is compatible with effective enhancement of morphine analgesia and reduction both of morphine tolerance acquisition and morphine dependence acquisition and expression. On the contrary, full alpha(2C)-activation appears advantageous in reducing morphine tolerance expression. Interestingly, the biological profile displayed by 4 (allyphenyline) and its eutomer (S)-(+)-4 has been found to be very unusual.

  DOI：

  10.1021/jm100977d

文献信息

• Fruitful Adrenergic α_2C-Agonism/α_2A-Antagonism Combination to Prevent and Contrast Morphine Tolerance and Dependence^,
  作者：Fabio Del Bello、Laura Mattioli、Francesca Ghelfi、Mario Giannella、Alessandro Piergentili、Wilma Quaglia、Claudia Cardinaletti、Marina Perfumi、Russell J. Thomas、Ugo Zanelli、Carla Marchioro、Michele Dal Cin、Maria Pigini

  DOI：10.1021/jm100977d

  日期：2010.11.11

  The functional in vitro study of the enantiomers of imidazolines 4-7 highlighted the role played by the nature of the ortho phenyl substituent in determining the preferred alpha(2C)-AR configuration. Indeed, the (S) enantiomers of 4-6 or (R) enantiomer of 7 behave as eutomers and activate this subtype as full agonists; the corresponding distomers are partial agonists. Because in clinical pain management with opioids alpha(2C)-AR agonists, devoid of the alpha(2A)-AR-mediated side effects, may represent an improvement over current therapies with clonidine like drugs, 4 and its enantiomers, showing alpha(2C)-agonism/alpha(2A)-Aantagonism, have been studied in vivo. The data suggest that partial alpha(2C)-activation is compatible with effective enhancement of morphine analgesia and reduction both of morphine tolerance acquisition and morphine dependence acquisition and expression. On the contrary, full alpha(2C)-activation appears advantageous in reducing morphine tolerance expression. Interestingly, the biological profile displayed by 4 (allyphenyline) and its eutomer (S)-(+)-4 has been found to be very unusual.