(+/-)-Biphenyline

• 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: (+/-)-Biphenyline
• 英文别名: 2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole；biphenyline；2-[1-(2-phenylphenoxy)ethyl]-4,5-dihydro-1H-imidazole
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: OGOLMGZJNRNULQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  2-(2-chloroethyl)imidazoline hydrochloride 、 邻苯基苯酚 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 9.0h， 以30%的产率得到(+/-)-Biphenyline
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation and High Antinociceptive Activity of (S)-(−)-2-[1-(Biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole

  摘要：

  A number of derivatives structurally related to cirazoline (1) were synthesized and studied with the purpose of modulating alpha(2)-adrenoreceptors selectivity versus both alpha(1)-adrenoreceptors and I-2 imidazoline binding sites. The most potent alpha(2)-agonist was 2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole (7), whose key pharmacophoric features closely matched those found in the alpha(2)-agonist 2-(3-exo-(3-phenylprop-1-yl)-2-exo-norborn,I)amino-2-oxazoline (15).(30) (S)-(-)-7 was the most potent of the two enantiomers, confirming the stereospecificity of the interaction with alpha(2)-adrenoreceptors. This eutomer was tested on two algesiometric paradigms and, because of the interaction with alpha(2)-adrenoreceptors, showed a potent and long-lasting antinociceptive activity, since it was abolished by the selective alpha(2)-antagonist RX821002.

  DOI：

  10.1021/jm0110082

文献信息

• α₂-Adrenoreceptors Profile Modulation and High Antinociceptive Activity of (<i>S</i>)-(−)-2-[1-(Biphenyl-2-yloxy)ethyl]-4,5-dihydro-1<i>H</i>-imidazole
  作者：Francesco Gentili、Pascal Bousquet、Livio Brasili、Mariangela Caretto、Antonio Carrieri、Monique Dontenwill、Mario Giannella、Gabriella Marucci、Marina Perfumi、Alessandro Piergentili、Wilma Quaglia、Carla Rascente、Maria Pigini

  DOI：10.1021/jm0110082

  日期：2002.1.1

  A number of derivatives structurally related to cirazoline (1) were synthesized and studied with the purpose of modulating alpha(2)-adrenoreceptors selectivity versus both alpha(1)-adrenoreceptors and I-2 imidazoline binding sites. The most potent alpha(2)-agonist was 2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole (7), whose key pharmacophoric features closely matched those found in the alpha(2)-agonist 2-(3-exo-(3-phenylprop-1-yl)-2-exo-norborn,I)amino-2-oxazoline (15).(30) (S)-(-)-7 was the most potent of the two enantiomers, confirming the stereospecificity of the interaction with alpha(2)-adrenoreceptors. This eutomer was tested on two algesiometric paradigms and, because of the interaction with alpha(2)-adrenoreceptors, showed a potent and long-lasting antinociceptive activity, since it was abolished by the selective alpha(2)-antagonist RX821002.