1-oxyl-2-(4-(dimethylamino)phenyl)-4,4,5,5-tetramethyl-2-imidazoline | 259093-33-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-oxyl-2-(4-(dimethylamino)phenyl)-4,4,5,5-tetramethyl-2-imidazoline
• 英文别名: 2-(4-dimethylaminophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole 1-oxyl
• CAS: 259093-33-9
• 化学式: C₁₅H₂₂N₃O
• 分子量: 260.359
• InChiKey: UJGQLGZHWGVFJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  19.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxyl-2-(4-(dimethylamino)phenyl)-4,4,5,5-tetramethyl-2-imidazoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以0.59 g的产率得到2-[(4-dimethylaminophenyl)]-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole 1-oxide
  参考文献：
  名称：

  1,2,3,7a-四氢咪唑并[1,2-b]异恶唑衍生物转化为异恶唑

  摘要：

  1,2,3,7a-四氢咪唑并[1,2-b]异恶唑衍生物与质子酸、苯甲酰氯、BF3和溴等亲电试剂反应生成异恶唑、2,2,3,3-四甲基氮丙啶和 2,3,3-三甲基丙烯-2-基胺衍生物。

  DOI：

  10.1007/s11172-007-0185-y
• 作为产物：
  描述：

  2,3-二甲基-2,3-二硝基丁烷 在 盐酸 、 氯化铵 、 lead dioxide 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.33h， 生成 1-oxyl-2-(4-(dimethylamino)phenyl)-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  Novel 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines: Synthesis, selectively analgesic action, and QSAR analysis

  摘要：

  Based on the knowledge that imidazoline can result in analgesic action due to its selective binding with the prostacyclin receptor, 20 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines (3a-t) were prepared in moderate yields. At 0.13 mmol/kg dose, their in vivo analgesic activities were evaluated after the mice were administered at 30, 60, 90, and 150 min. Compared with the pain threshold (12.27 +/- 9.56-17.71 +/- 7.00%) of normal saline (NS) receiving mice, the pain threshold (23.42 +/- 8.14% to 102.58 +/- 10.66%) of 3a-t receiving mice increases significantly. Considering a prostacyclin receptor targeting analgesic agent usually had bleeding action and to appraise the bleeding risk, the in vivo tail bleeding time of 1.30 mmol/kg 3a-t receiving mice was found to be ranged from 116.3 +/- 8.2 s to 120.3 +/- 9.2 s, which was substantially equal to that (117.8 +/- 8.4 s to 119.0 +/- 8.6 s) of NS receiving mice. Based on the possibility of imidazoline acting as vasodilator, the in vitro vasorelaxations of 3a-t were tested using the rat aortic strip model. When the aortic strip contracted by noradrenaline (NE, final concentration 10(-7) mol/l) was treated with 3a-t (final concentration 5 x 10(-4) mol/l), only lower percentage inhibitions (6.55 +/- 5.70-37.40 +/- 4.07%) were recorded, implying that the vasorelaxation of 3a-t was neglectable. By selecting appropriate molecular descriptors generated from e-dragon server, the QSAR model of the analgesic activities of 3a-t was constructed using the multiple linear regression method. The established QSAR model showed reasonable accuracy and thus it is promising to be used for screening new 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazoline derivatives as analgesic agents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.023

文献信息

• Transformation of 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives into isoxazoles
  作者：N. V. Chukanov、S. A. Popov、G. V. Romanenko、V. A. Reznikova

  DOI：10.1007/s11172-007-0185-y

  日期：2007.6

  The reactions of 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives with electrophilic reagents, such as protic acids, benzoyl chloride, BF3, and bromine, produce isoxazole, 2,2,3,3-tetramethylaziridine, and 2,3,3-trimethylpropen-2-ylamine derivatives.

  1,2,3,7a-四氢咪唑并[1,2-b]异恶唑衍生物与质子酸、苯甲酰氯、BF3和溴等亲电试剂反应生成异恶唑、2,2,3,3-四甲基氮丙啶和 2,3,3-三甲基丙烯-2-基胺衍生物。
• Novel 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines: Synthesis, selectively analgesic action, and QSAR analysis
  作者：Ming Zhao、Zheng Li、Li Peng、Yu-Rong Tang、Chao Wang、Ziding Zhang、Shiqi Peng

  DOI：10.1016/j.bmc.2007.02.023

  日期：2007.4

  Based on the knowledge that imidazoline can result in analgesic action due to its selective binding with the prostacyclin receptor, 20 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines (3a-t) were prepared in moderate yields. At 0.13 mmol/kg dose, their in vivo analgesic activities were evaluated after the mice were administered at 30, 60, 90, and 150 min. Compared with the pain threshold (12.27 +/- 9.56-17.71 +/- 7.00%) of normal saline (NS) receiving mice, the pain threshold (23.42 +/- 8.14% to 102.58 +/- 10.66%) of 3a-t receiving mice increases significantly. Considering a prostacyclin receptor targeting analgesic agent usually had bleeding action and to appraise the bleeding risk, the in vivo tail bleeding time of 1.30 mmol/kg 3a-t receiving mice was found to be ranged from 116.3 +/- 8.2 s to 120.3 +/- 9.2 s, which was substantially equal to that (117.8 +/- 8.4 s to 119.0 +/- 8.6 s) of NS receiving mice. Based on the possibility of imidazoline acting as vasodilator, the in vitro vasorelaxations of 3a-t were tested using the rat aortic strip model. When the aortic strip contracted by noradrenaline (NE, final concentration 10(-7) mol/l) was treated with 3a-t (final concentration 5 x 10(-4) mol/l), only lower percentage inhibitions (6.55 +/- 5.70-37.40 +/- 4.07%) were recorded, implying that the vasorelaxation of 3a-t was neglectable. By selecting appropriate molecular descriptors generated from e-dragon server, the QSAR model of the analgesic activities of 3a-t was constructed using the multiple linear regression method. The established QSAR model showed reasonable accuracy and thus it is promising to be used for screening new 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazoline derivatives as analgesic agents. (c) 2007 Elsevier Ltd. All rights reserved.