1-oxyl-2-(3-nitrophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline | 117566-84-4

• 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: 1-oxyl-2-(3-nitrophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline
• 英文别名: 2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl；2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide
• CAS: 117566-84-4
• 化学式: C₁₃H₁₆N₃O₄
• 分子量: 278.288
• InChiKey: ZTLHUBLYHAGCHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 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：
  78.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxyl-2-(3-nitrophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline 在 nitric oxide 作用下， 以 正己烷 、 氯仿 为溶剂， 生成 1-oxyl-2-(3-nitrophenyl)-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  取代基对2-（取代苯基）-4,5-二氢-4,4,5,5-四甲基咪唑-1-氧基3-氧化物与一氧化氮反应的影响：一项实验和MNDO研究

  摘要：

  使用液相色谱法测定了2-（取代的苯基）-4,5-二氢-4,4,5,5-四甲基咪唑-1-氧基3-氧化物与一氧化氮的氧转移反应的相对速率常数（ hplc）。哈米特ρ值（–0.37）表明给电子取代基有利于反应。这可以通过包括电子转移到一氧化氮的机制来解释，并且可以通过半经验MNDO方法计算出的硝酰氧的前沿轨道能量和电子密度来合理化。

  DOI：

  10.1039/p29880000795
• 作为产物：
  描述：

  2,3-二甲基-2,3-二硝基丁烷 在 氯化铵 、 lead dioxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 35.33h， 生成 1-oxyl-2-(3-nitrophenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline
  参考文献：
  名称：

  作为自由基清除剂的新型2-取代硝酰基硝基氧化合物：合成，生物学评估和结构-活性关系。

  摘要：

  为了开发具有增强的自由基清除剂性能的更有效的小分子，我们设计并合成了一系列硝酰基硝基氧衍生物4a-h。基于Ach诱导的血管舒张测定法发现了前导化合物4f。基于该支架的进一步化学修饰提供了一系列新的2-取代的苯基亚硝酰基硝基氧化物衍生物6a-s。基于PC12细胞存活测定法，新合成的化合物6a-s具有改善的自由基清除剂的活性。就NO，H（2）O（2）和OH的清除能力而言，化合物6g，n，o和s是一些最有效的化合物。2-取代的苯基亚硝基硝基氮氧化物具有较高的自由基清除活性，带有给电子基团（EDG）。相比之下，吸电子基团（EWG）引入芳环导致其自由基清除活性急剧下降。这些结果表明，芳香环的给电子基团（EDG）可能是影响这些化合物清除自由基行为的重要因素，清除自由基的能力很大程度上取决于苯环的位置和电子性质。取代基。新型的2-取代的硝酰基氮氧化物的增强的自由基清除能力可能是对抗ROS（活性氧）/ R

  DOI：

  10.1016/j.bmc.2006.04.016

文献信息

• Synthesis and Reactions of New Nitronyl Nitroxides
  作者：Tamás Kálai

  DOI：10.1055/s-1997-1311

  日期：1997.9

  Various new 2-substituted 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-yloxyl 3-oxide mono- 1b, 7, 13a,b, 14, 15, 16, 17, 22 and biradicals 8, 9 were prepared. The nitronyl nitroxide functions were selectively reduced by Fe/HOAc to 1-hydroxyimidazoline derivatives 3b, 11, 21. The reductions by Zn/HCl led to imidazolines 4, 12. The nitronyl nitroxide functions remained inert when the 2-phenyl compounds was nitrated by H2SO4/HNO3 to give nitrophenyl nitronyl nitroxide derivatives 13a,b, 14.

  合成了多种新型2取代的4,4,5,5-四甲基-4,5-二氢-1H-咪唑-1-氧基3-氧化物单体1b、7、13a、b、14、15、16、17、22以及双自由基8、9。通过Fe/HOAc选择性还原了亚硝基氮氧化物，生成了1-羟基咪唑啉衍生物3b、11、21。使用Zn/HCl还原得到咪唑啉4、12。在用H2SO4/HNO3对2-苯基化合物进行硝化时，亚硝基氮氧化物功能保持惰性，生成了硝基苯亚硝基氮氧化物衍生物13a、b、14。
• Four new Cu-coordination compounds based on different nitronyl nitroxide radicals: Structural design and magneto-structural correlations
  作者：Ya-Li Wang、Yuan-Yuan Gao、Ming-Fang Yang、Tao Gao、Yue Ma、Qing-Lun Wang、Dai-Zheng Liao

  DOI：10.1016/j.poly.2013.05.036

  日期：2013.9

  . The X-ray crystal structure analyses show that complexes 1 and 2 have similar centrosymmetric five-spin structures built by three Cu(hfac)2 units bridged by two nitroxide ligands through their NO groups. While complex 3 consists of isolated molecule where the nitronyl nitroxide radical acts as chelating ligand towards copper(II), and complex 4 is a rare mononuclear tri-spin compound, in which central

  摘要合成了四种具有不同硝酰基氮氧自由基的新型铜（II）配合物，其结构和磁学特征为[[Cu（hfac）2）3（NITPh-3-Br-4-OMe）2]（1），[[ Cu（hfac）2）3（NITPyOMe）2]（2），[Cu（hfac）2（2-QNNN）]（3）和[Cu（hfac）2（NITmNO2）2]（4）（hfac =六氟-乙酰丙酮酸酯;且NITPh-3-Br-4-OMe = 2-3'-Br-4'-甲氧基苯基-4,4,5,5-四甲基咪唑啉-1-氧基-3-氧化物，NITPyOMe = 2-4' -甲氧基-3'-吡啶基-4,4,5,5-四甲基咪唑啉-1-氧基-3-氧化物，2-QNNN = 2-2'-喹啉基-4,4,5,5-四甲基咪唑啉-1 -3-氧-3-氧化物，NITmNO 2 ＝ 2-（3-硝基苯基）-4,4,5,5-四甲基-咪唑啉-1-氧-3-氧化物）。X射线晶体结构分析表明，配合物1和
• Synthesis, crystal structures and magnetic properties of copper(II) complexes with nitronyl nitroxide
  作者：Lei Zhang、Su-Qi Li、Bai-Wang Sun、Dai-Zheng Liao、Zong-Hui Jiang、Shi-Ping Yan、Geng-Lin Wang、Xin-Kan Yao、Hong-Gen Wang

  DOI：10.1016/s0277-5387(98)00356-8

  日期：1999.1

  (NITmNO 2 ) (II), where pfpr=pentafluoropropionate, hfac=hexafluoroacetylacetonate and NITmNO 2 =2-(3-nitrophenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide, have been synthesized. Compound (I) is the first example of copper (II)–nitroxide complexes bridged by pfpr. Its structure consists of binuclear units with the tetrakis(pentafluoropropionate) bridging two copper ions. Each copper ion has a distorted

  摘要两种新的式[Cu（pfpr）2（NITmNO 2）] 2（I）和Cu（hfac）2（NITmNO 2）（II）的加合物，其中pfpr =五氟丙酸酯，hfac =六氟乙酰丙酮酸酯和NITmNO 2 = 2-（已经合成了3-硝基苯基）-4,4,5,5-四甲基咪唑啉-1-氧基-3-氧化物。化合物（I）是由pfpr桥接的铜（II）-硝基氧化物络合物的第一个实例。它的结构由双核单元和四（五氟丙酸酯）桥联两个铜离子组成。每个铜离子具有扭曲的三角-双锥体配位。化合物（II）是单核络合物，具有五配位扭曲的方金字塔形环境。可变温度磁化率表明，化合物（I）的铜离子与自由基之间存在反铁磁相互作用，并且化合物（II）是抗磁性的。
• 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.