4,4,5,5-tetramethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazol-1-ol | 735278-75-8

• 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: 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazol-1-ol
• 英文别名: 1-Hydroxy-4,4,5,5-tetramethyl-2-(4-nitrophenyl)imidazole
• CAS: 735278-75-8
• 化学式: C₁₃H₁₇N₃O₃
• 分子量: 263.296
• InChiKey: YRWHJCQVVUFXNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 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：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazol-1-ol 以 乙醚 、 氯仿 为溶剂， 反应 48.5h， 生成 1-(acetyloxy)-3,4,4,5,5-pentamethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazol-3-ium methylsulphate
  参考文献：
  名称：

  Aminonitrone-N-hydroxyaminoimine tautomeric equilibrium in the series of 1-hydroxy-2-imidazolines

  摘要：

  A series of 2-substituted 1-hydroxy-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoles have been synthesized. Various effects on the state of the aminonitrone-N-hydroxyaminoimine tautomeric equilibrium, including solvent effects and substituent effect in the 2 position of heterocycle, have been studied. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.02.028
• 作为产物：
  描述：

  1,3-dihydroxy-2-(4-nitrophenyl)-4,4,5,5-tetramethylimidazolidine 在 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以166 mg的产率得到4,4,5,5-tetramethyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazol-1-ol
  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

文献信息

• Aminonitrone-N-hydroxyaminoimine tautomeric equilibrium in the series of 1-hydroxy-2-imidazolines
  作者：Sergey A. Popov、Rodion V. Andreev、Galina V. Romanenko、Viktor I. Ovcharenko、Vladimir A. Reznikov

  DOI：10.1016/j.molstruc.2004.02.028

  日期：2004.7

  A series of 2-substituted 1-hydroxy-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoles have been synthesized. Various effects on the state of the aminonitrone-N-hydroxyaminoimine tautomeric equilibrium, including solvent effects and substituent effect in the 2 position of heterocycle, have been studied. (C) 2004 Elsevier B.V. All rights reserved.
• 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
  作者：Ming Zhao、Zheng Li、Li Peng、Yu-Rong Tang、Chao Wang、Ziding Zhang、Shiqi Peng

  DOI：10.1016/j.ejmech.2007.07.007

  日期：2008.5

  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.