2-[(3-hydroxy-4,4,5,5-tetramethylimidazoline)-2-yl]phenol | 899419-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(3-hydroxy-4,4,5,5-tetramethylimidazoline)-2-yl]phenol
• 英文别名: 2-(1-Hydroxy-4,4,5,5-tetramethylimidazol-2-yl)phenol
• CAS: 899419-40-0
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: JYEYTRMYMQVPLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3-hydroxy-4,4,5,5-tetramethylimidazoline)-2-yl]phenol 、 copper diacetate 在 NH₄OH 、 PbO₂ 作用下， 以 甲醇 、 水 为溶剂， 以51%的产率得到copper(II) bis[2-[(4,4,5,5-tetramethylimidazoline-1-oxyl)-2-yl]phenolate]
  参考文献：
  名称：

  Synthesis and magnetic properties of an iminonitroxide-substituted phenolate–Cu complex

  摘要：

  A new spin-chelate, iminonitroxide-substituted phenolate-copper complex (1), was designed and prepared. The structure of the complex I was considerably deviated from a square-planar geometry. The dihedral angle between the two planes defined by a set of copper, oxygen and nitrogen atoms was about 41degrees. The complex was found to have a relatively strong ferromagnetic interaction and a weaker antiferromagnetic interaction: J/k(B) = +250 K and theta = -17 K using a three-spin model. The ferromagnetic interaction was assigned to the intramolecular interaction between the copper atom and the iminonitroxide. The antiferromagnetic interaction was assigned as an intermolecular interaction. These assignments were supported by susceptibility measurements for the diluted sample in polyvinyl chloride (PVC) film. The antiferromagnetic interaction was tentatively assigned due to the observed short intermolecular contacts between the C5 and 01 atoms or between the H5 and 01 atoms. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(03)00190-6
• 作为产物：
  描述：

  1,3-dihydroxy-2-(2'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine 在 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以115 mg的产率得到2-[(3-hydroxy-4,4,5,5-tetramethylimidazoline)-2-yl]phenol
  参考文献：
  名称：

  A new class of analgesic agents toward prostacyclin receptor inhibition: Synthesis, biological studies and QSAR analysis of 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines

  摘要：

  By studying the structural similarity of analgesic imidazolines and 2-phenylnitronyl nitroxides, 20 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines (2a-t) were newly synthesized as selective antagonists of prostacyclin receptor (IP receptor). In the in vivo tail-flick assay, 2a-t (dose, 0.13 mmol/kg) receiving mice showed increased pain thresholds ranging from 20.52 +/- 7.25% to 90.94 +/- 11.97%, which were significantly higher than that ranged from 12.27 +/- 9.56% to 17.71 +/- 7.00% shown by normal saline (NS) receiving mice. In the in vivo tail bleeding assay, 2a-t (dose, 1.30 mmol/kg) receiving mice gave a bleeding time ranging from 116.3 +/- 8.0 s to 119.6 +/- 7.1 s, and NS receiving mice gave a bleeding time ranging from 116.7 +/- 7.5 s to 119.1 +/- 8.7 s, which were at a substantially equal level. These observations imply that no bleeding risk occurred even when 10-fold dose of analgesic assay was used. In the in vitro vasorelaxation assay, it was found that when the aortic strip contracted by noradrenaline (NE, final concentration, 10(-7) M) was treated with the solution of 2a-t in NS (final concentration, 5 x 10(-3) M) only lower percentage inhibitions ranged from 6.63 +/- 2.72% to 46.28 +/- 2.63% were recorded. Relatively higher concentration of 2a-t (5 x 10(-3) M) and relatively lower percentage inhibitions (13 of 20 less than 23.27 +/- 3.47%) suggest that 2a-t exhibit few vasodilation activity. To shed some light on the potential analgesic mechanisms of 2a-t, moreover, a QSAR analysis was carried out by using the multiple linear regression method. Taken altogether, the current study confirms that as selective antagonist of IP receptor 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazoline may be a promising lead compound of analgesic agent without cardiovascular and bleeding side effects. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.07.007