2-(2'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl | 163461-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl
• 英文别名: 1-oxyl-2-(2-hydroxyphenyl)-3-oxo-4,4,5,5-tetramethyl-2-imidazoline；2-(2-hydroxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide
• CAS: 163461-39-0
• 化学式: C₁₃H₁₇N₂O₃
• 分子量: 249.29
• InChiKey: ROLOZZUKVIRUPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以76%的产率得到2-(2-hydroxyphenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl
  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
• 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 2-(2'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl
  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

• Novel 2-substituted nitronyl nitroxides as free radical scavengers: Synthesis, biological evaluation and structure–activity relationship
  作者：Yihui Wu、Lanrong Bi、Wei Bi、Zeng Li、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2006.04.016

  日期：2006.8

  nitroxide derivatives 4a-h. A lead compound 4f was discovered based on Ach-induced vascorelaxation assay. Further chemical modification based on this scaffold provided a new series of 2-substituted phenylnitronyl nitroxide derivatives 6a-s. The newly synthesized compounds 6a-s possess improved radical scavenger's activity based on PC12 cell survival assay. Compounds 6g,n,o, and s are some of the most

  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
• Dinuclear lanthanide complexes bridged by nitronyl nitroxide radical ligands with 2-phenolate groups: structure and magnetic properties
  作者：Xuelan Mei、Xiufeng Wang、Juanjuan Wang、Yue Ma、Licun Li、Daizheng Liao

  DOI：10.1039/c3nj00739a

  日期：——

  Three novel binuclear lanthanide–radical complexes [Ln2(acac)4(NITPhO)2] (Ln(III) = Gd 1, Eu 2, Dy 3; acac = acetylacetonato and NITPhOH = 2-(2′-hydroxyphenyl)-4,4,5,5-tetramethyl-imidazoline-1-oxyl-3-oxide) have been achieved. These compounds possess dinuclear structure in which two radical ligands link two lanthanide ions through their phenoxo-O atoms. Magnetic studies show that the Gd(III) ion interacts

  三种新颖的双核镧系-自由基配合物[Ln 2（acac）4（NITPhO）2 ]（Ln（III）= Gd 1，Eu 2，Dy 3； acac =乙酰丙酮和NITPhOH = 2-（2'-羟基苯基）-4已经获得了（4,5,5-四甲基-咪唑啉-1-氧基-3-氧化物）。这些化合物具有双核结构，其中两个自由基配体通过其苯氧-O原子连接两个镧系离子。磁性研究表明，Gd（III离子与直接键合的NO基团发生铁磁相互作用，而两个镧系离子之间通过两个苯氧羰基进行的磁相互作用则是反铁磁的。没有发现Dy络合物的频率相关的异相信号，这表明金属中心周围的配体场在调节镧系元素的磁弛豫中起关键作用。
• Design, synthesis and biological evaluation of novel nitric oxide donors with antioxidative activity
  作者：Jing Liang、Pengfei Zhang、Hongyan Yang、Ying Zhang、Tuanli Yao、Keke Liu、Yukun Wang、Xing Zhang、Xiangyang Qin

  DOI：10.1016/j.ejmech.2022.114331

  日期：2022.6

  of novel epimeric nitroxide-nitrate conjugates (15(S) and 15(R)), which had pharmacophore connections. We also synthesized 8 NIT radicals without 5-ISMN in order to compare the activities of these novel nitric oxide donors. Several dual-acting nitroxide-based nitrate conjugates showed the ability to release NO and cause anti-oxidant effects in human umbilical vein endothelial cells. Among these conjugates

  活性氧（ROS）是有机硝酸盐药物耐受和内皮功能障碍的主要原因。为了清除 ROS 并维持硝酸盐的治疗效果，我们将 NIT 型氮氧化物和 5-ISMN 结合，设计并合成了 10 种新型双作用硝酸盐分子。其中包括两种新型差向异构氮氧化物-硝酸盐偶联物（15( S )和15( R ))，它具有药效团连接。我们还合成了 8 个不含 5-ISMN 的 NIT 自由基，以比较这些新型一氧化氮供体的活性。几种基于双效氮氧化物的硝酸盐缀合物显示出在人脐静脉内皮细胞中释放 NO 并引起抗氧化作用的能力。在这些缀合物中，15( S )表现出最显着的促血管舒张作用。在血管紧张素 II 输注诱导的高血压小鼠中，15( S )治疗 4 周降低了收缩压和舒张压，并改善了孤立胸主动脉的血管内皮和平滑肌功能。此外，小鼠血管结构得到恢复，血管氧化应激降低。结果表明，这些新型一氧化氮供体可用作治疗血管疾病的潜在药物。因此，结合使用抗氧化剂和
• Ligand substitution effect on single-molecule magnet behavior in dinuclear dysprosium complexes with radical functionalized phenol as bridging ligands
  作者：Ruina Liu、Congming Zhang、Licun Li、Daizheng Liao、Jean-Pascal Sutter

  DOI：10.1039/c2dt31310c

  日期：——

  compounds are phenoxo-O bridged binuclear complexes with the radical unit of a ligand coordinated to a single Dy. The Ln centers exhibit a heptacoordinated environment. Despite having very similar structures, these compounds exhibit distinct magnetic behaviors. Compound 1 shows slow relaxation of its magnetization indicating single-molecule magnet behavior, while no frequency-dependent out-of-phase signals

  Dy（hfac）3 ·2H 2 O（hfac =六氟乙酰丙酮）与2-（2-羟苯基）亚硝酰基硝基氧化物（NITPhOH）和2-（5-溴-2-羟苯基）亚硝酰基硝基氧化物（NIT5BrPhOH）反应生成[Dy 2（hfac）4（NITPhO）2 ] 1和[Dy 2（hfac）4（NIT5BrPhO）2 ] 2分别。这些化合物是苯氧-O桥联的双核络合物，配体的自由基单元与单个Dy配位。Ln中心展示了七坐标环境。尽管具有非常相似的结构，但这些化合物仍表现出不同的磁行为。化合物1显示出其磁化缓慢弛豫，表明单分子磁体行为，而对于复合物2未发现与频率相关的异相信号。这种差异很可能是由卤素取代引起的电子效应引起的。
• Bisnitronyl nitroxides bridged by tetra(ethyleneoxy) sensing metal ions spectroscopically and electrochemically
  作者：Yanxin Yu、Deqing Zhang、Guanxin Zhang、Zhiyong Wang、Daoben Zhu

  DOI：10.1016/j.tetlet.2006.03.061

  日期：2006.5

  Compound 1 containing two nitronyl nitroxide units bridged by tetra(ethyleneoxy) was designed and synthesized for sensing metal ions, by taking the features of nitronyl nitroxides: a chromophore showing absorption in visible range, reversible oxidation/reduction and coordination to metal ions. The absorption spectrum Of 1 was altered markedly upon mixing with a few rare earth metal ions and some transition metal ions. Moreover, the oxidation potential of 1 was shifted to more positive range in the presence of metal ions including Pb2+, Ba2+, and Ca2+. Thus, compound 1 can sense metal ions both spectroscopically and electrochemically, (c) 2006 Elsevier Ltd. All rights reserved.