2-phenanthren-9-yl-4,5-dihydro-1H-imidazole | 66051-83-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-phenanthren-9-yl-4,5-dihydro-1H-imidazole
• 英文别名: 2-phenanthren-9-yl-4,5-dihydro-1H-imidazole
• CAS: 66051-83-0
• 化学式: C₁₇H₁₄N₂
• 分子量: 246.312
• InChiKey: KSHHDMBEBWKJAO-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  456.3±28.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对氯苯甲酸甲酯 、 2-phenanthren-9-yl-4,5-dihydro-1H-imidazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以39%的产率得到20-(4-Chlorophenyl)-16,19-diazapentacyclo[12.6.0.02,7.08,13.015,19]icosa-1(14),2,4,6,8,10,12,15-octaen-20-ol
  参考文献：
  名称：

  Benzo- and Cyclohexanomazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol (1), homomazindol (2), and bishomomazindol (3) derivatives with a benzo or cyclohexano ring fused At various sites were prepared as part of an SAR study to determine the effect of increased aliphatic and aromatic lipophilicity on selected in vitro assays used to identify potential cocaine-like and cocaine antagonism activity. Very good (IC50 = 2-3 nM) inhibition of [H-3] WIN 35,428 and [I-125] RTI-55 binding on rat or guinea pig striatal membranes and HEK cells expressing cDNA for the human dopamine transporter (HEK-hDAT) was shown by the 8,9-benzomazindol 25 and 9,10-benzohomomazindol 28. All new compounds were weaker inhibitors of [H-3] DA uptake in HEK-hDAT cells than 1 and 2. No improvement in the binding selectivity ratio (SERT/DAT and NET/DAT) was found when compared to 2. Compounds 25 and 28 showed a considerable increase versus 1 in uptake/binding discrimination ratios at the DAT (311.0 and 182.1 vs 0.9), SERT (33.6 and 127.3 vs 1.9), and NET (7.3 and 10.0 vs 0.3).

  DOI：

  10.1021/jm010301z
• 作为产物：
  描述：

  9-腈菲 、 乙二胺 在 对甲苯磺酸 作用下， 以 乙二醇 为溶剂， 反应 48.0h， 以50%的产率得到2-phenanthren-9-yl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Benzo- and Cyclohexanomazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol (1), homomazindol (2), and bishomomazindol (3) derivatives with a benzo or cyclohexano ring fused At various sites were prepared as part of an SAR study to determine the effect of increased aliphatic and aromatic lipophilicity on selected in vitro assays used to identify potential cocaine-like and cocaine antagonism activity. Very good (IC50 = 2-3 nM) inhibition of [H-3] WIN 35,428 and [I-125] RTI-55 binding on rat or guinea pig striatal membranes and HEK cells expressing cDNA for the human dopamine transporter (HEK-hDAT) was shown by the 8,9-benzomazindol 25 and 9,10-benzohomomazindol 28. All new compounds were weaker inhibitors of [H-3] DA uptake in HEK-hDAT cells than 1 and 2. No improvement in the binding selectivity ratio (SERT/DAT and NET/DAT) was found when compared to 2. Compounds 25 and 28 showed a considerable increase versus 1 in uptake/binding discrimination ratios at the DAT (311.0 and 182.1 vs 0.9), SERT (33.6 and 127.3 vs 1.9), and NET (7.3 and 10.0 vs 0.3).

  DOI：

  10.1021/jm010301z

文献信息

• Imidazoline receptors: Qualitative structure-activity relationships and discovery of tracizoline and benazoline. Two ligands with high affinity and unprecedented selectivity
  作者：Maria Pigini、Pascal Bousquet、Angelo Carotti、Monique Dontenwill、Mario Giannella、Roberta Moriconi、Alessandro Piergentili、Wilma Quaglia、Seyed K. Tayebati、Livio Brasili

  DOI：10.1016/s0968-0896(97)00009-6

  日期：1997.5

  characterize imidazoline (I) receptors have been carried out with non-selective or poorly selective ligands prompted us to undertaken research aimed at developing selective ligand(s). In previous work using, as a starting point, cirazoline I, a potent alpha 1-adrenergic receptor agonist that also binds to I receptors, we showed that removal of the cyclopropyl ring (2) retains high affinity for I2 receptors

  观察到所有表征咪唑啉（I）受体的尝试都是使用非选择性或选择性差的配体进行的，这促使我们进行了旨在开发选择性配体的研究。在以前的研究中，以环丙唑啉I为起点，环丙唑啉I是一种也与I受体结合的有效的α1-肾上腺素能受体激动剂，我们发现环丙基环（2）的去除保留了对I2受体的高亲和力，同时降低了α1-肾上腺素激动剂活性。但是，人们认为这种残留的α1肾上腺素激动剂活性虽然适度，但可能会降低化合物2的效用，我们现在报告我们在这一领域的不断努力。从化合物2开始，我们首先通过等位置换消除了α1-激动剂成分，然后，通过对化合物7的构象限制，成功发现了曲西唑啉（9）和苯并唑啉（12）。这两个新的配体具有高亲和力（分别为pKi值8.74和9.07），并且对alpha 2-（I2 / alpha 2 7,762和18,621）和alpha 1-（I2 / alpha 1 2,344和2,691）肾上腺素能受体具有前
• Benzo- and Cyclohexanomazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter
  作者：William J. Houlihan、Umer F. Ahmad、Judith Koletar、Lawrence Kelly、Leonard Brand、Theresa A. Kopajtic

  DOI：10.1021/jm010301z

  日期：2002.9.1

  A series of mazindol (1), homomazindol (2), and bishomomazindol (3) derivatives with a benzo or cyclohexano ring fused At various sites were prepared as part of an SAR study to determine the effect of increased aliphatic and aromatic lipophilicity on selected in vitro assays used to identify potential cocaine-like and cocaine antagonism activity. Very good (IC50 = 2-3 nM) inhibition of [H-3] WIN 35,428 and [I-125] RTI-55 binding on rat or guinea pig striatal membranes and HEK cells expressing cDNA for the human dopamine transporter (HEK-hDAT) was shown by the 8,9-benzomazindol 25 and 9,10-benzohomomazindol 28. All new compounds were weaker inhibitors of [H-3] DA uptake in HEK-hDAT cells than 1 and 2. No improvement in the binding selectivity ratio (SERT/DAT and NET/DAT) was found when compared to 2. Compounds 25 and 28 showed a considerable increase versus 1 in uptake/binding discrimination ratios at the DAT (311.0 and 182.1 vs 0.9), SERT (33.6 and 127.3 vs 1.9), and NET (7.3 and 10.0 vs 0.3).