(R)-(-)-2'-(1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy)biphenyl-3-amine hydrogen oxalate | 1253421-36-1

• 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: (R)-(-)-2'-(1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy)biphenyl-3-amine hydrogen oxalate
• 英文别名: 3-[2-[(1R)-1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy]phenyl]aniline;oxalic acid
• CAS: 1253421-36-1
• 化学式: C₂H₂O₄*C₁₇H₁₉N₃O
• 分子量: 371.393
• InChiKey: WHVWLDTXJBFUQZ-UTONKHPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2'-(1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy)biphenyl-3-amine hydrogen oxalate 在 硫酸 、 sodium nitrite 、 尿素 、 copper(I) oxide 作用下， 以 水 为溶剂， 反应 0.5h， 以39%的产率得到(R)-(+)-2'-[1-(4,5-dihydro-1H-imidazol-2-yl)-ethoxy]-biphenyl-3-ol
  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
• 作为产物：
  描述：

  (+)-m-Nitrobiphenyline 、 草酸 在 5% palladium on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 8.0h， 生成 (R)-(-)-2'-(1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy)biphenyl-3-amine hydrogen oxalate
  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.