3-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-vinyl]-pyridine | 474310-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-vinyl]-pyridine
• 英文别名: 3-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)ethenyl]pyridine
• CAS: 474310-65-1
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: IWXABZVIIOVEBR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-vinyl]-pyridine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 以95%的产率得到3-[2-(4,5-dihydro-1H-imidazol-2-yl)-ethyl]-pyridine
  参考文献：
  名称：

  Novel Ligands Rationally Designed for Characterizing I₂−Imidazoline Binding Sites Nature and Functions

  摘要：

  The study of two series of 2-aryl-ethylen-imidazolines 3-7 and 8-12 inspired by I(2)-IBS ligands phenyzoline (1) and diphenyzoline (2), respectively, confirmed the interesting "positive" or "negative" morphine analgesia modulation displayed by their corresponding leads and demonstrated that these effects might be correlated with morphine tolerance and dependence, respectively. By comparative examination of rationally designed compounds, some analogies between binding site cavity of I(2)-IBS proteins and alpha(2C)-adrenoreceptor emerged.

  DOI：

  10.1021/jm800400k
• 作为产物：
  描述：

  2-甲基咪唑啉 、 3-吡啶甲醛 在 甲酸丁酯 作用下， 生成 3-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-vinyl]-pyridine
  参考文献：
  名称：

  Homoazanicotine:  A Structure-Affinity Study for Nicotinic Acetylcholine (nACh) Receptor Binding

  摘要：

  We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homo-azanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicotinic (K-i = 7.8 nM) vs muscarinic (K-i > 10 000 nM) acetylcholinergic receptors, we examined its structure-affinity relationships for nACh receptor binding. The features investigated included the influence of (i) the composition of connector that separates the two rings, (ii) the N-methyl group, (iii) the ring opening of the imidazoline ring, (iv) the pyridine nitrogen atom, and (v) the aromatization of the imidazoline ring on nACh receptor affinity. As with nicotine, the parent structure seems optimal and most structural changes reduce nACh receptor affinity. Also, as with nicotine analogues, alteration of the spacer group influences affinity in a manner that is somewhat different than that seen with the parent structure.

  DOI：

  10.1021/jm020188s

文献信息

• Homoazanicotine:  A Structure-Affinity Study for Nicotinic Acetylcholine (nACh) Receptor Binding
  作者：G. Ferretti、M. Dukat、M. Giannella、A. Piergentili、M. Pigini、W. Quaglia、M. I. Damaj、B. R. Martin、R. A. Glennon

  DOI：10.1021/jm020188s

  日期：2002.10.1

  We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homo-azanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicotinic (K-i = 7.8 nM) vs muscarinic (K-i > 10 000 nM) acetylcholinergic receptors, we examined its structure-affinity relationships for nACh receptor binding. The features investigated included the influence of (i) the composition of connector that separates the two rings, (ii) the N-methyl group, (iii) the ring opening of the imidazoline ring, (iv) the pyridine nitrogen atom, and (v) the aromatization of the imidazoline ring on nACh receptor affinity. As with nicotine, the parent structure seems optimal and most structural changes reduce nACh receptor affinity. Also, as with nicotine analogues, alteration of the spacer group influences affinity in a manner that is somewhat different than that seen with the parent structure.
• Novel Ligands Rationally Designed for Characterizing I₂−Imidazoline Binding Sites Nature and Functions
  作者：Francesco Gentili、Claudia Cardinaletti、Cristian Vesprini、Francesca Ghelfi、Aniket Farande、Mario Giannella、Alessandro Piergentili、Wilma Quaglia、Laura Mattioli、Marina Perfumi、Alan Hudson、Maria Pigini

  DOI：10.1021/jm800400k

  日期：2008.8.1

  The study of two series of 2-aryl-ethylen-imidazolines 3-7 and 8-12 inspired by I(2)-IBS ligands phenyzoline (1) and diphenyzoline (2), respectively, confirmed the interesting "positive" or "negative" morphine analgesia modulation displayed by their corresponding leads and demonstrated that these effects might be correlated with morphine tolerance and dependence, respectively. By comparative examination of rationally designed compounds, some analogies between binding site cavity of I(2)-IBS proteins and alpha(2C)-adrenoreceptor emerged.