3-aminomethyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl | 78140-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-aminomethyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl
• 英文别名: 3-(aminomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy
• CAS: 78140-48-4
• 化学式: C₉H₁₇N₂O
• 分子量: 169.247
• InChiKey: SLGAGQTYYXSFGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  30.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-aminomethyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl 在 mercury(II) oxide 作用下， 以 吡啶 、 乙醚 、 苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Nitroxyls; VIII¹. Synthesis of Nitroxylphosphinimines; A Convenient Route to Amine, Isothiocyanate, Aminocarbonylaziridine, and Carbodiimide Nitroxyls

  摘要：

  DOI：

  10.1055/s-1981-29370
• 作为产物：
  描述：

  以 乙醇 为溶剂， 反应 10.0h， 生成 3-aminomethyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl
  参考文献：
  名称：

  Nitroxyls; VIII¹. Synthesis of Nitroxylphosphinimines; A Convenient Route to Amine, Isothiocyanate, Aminocarbonylaziridine, and Carbodiimide Nitroxyls

  摘要：

  DOI：

  10.1055/s-1981-29370

文献信息

• Synthesis of new spin labels for Cu-free click conjugation
  作者：Tamás Kálai、Mark R. Fleissner、József Jekő、Wayne L. Hubbell、Kálmán Hideg

  DOI：10.1016/j.tetlet.2011.03.077

  日期：2011.5

  New pyrroline nitroxides attached to a terminal acetylenic sulfone, a dibenzocyclooctyne or a cyclooctyne carboxylic acid were synthesized and tested in Cu-free click reactions to conjugate these new spin labels with 4-azido-TEMPO, azidophenylalanine and an azidophenylalanine-containing protein.

  合成并连接到末端乙炔砜，二苯并环辛炔或环辛炔羧酸的新吡咯啉氮氧化物，并在无铜点击反应中进行了测试，以使这些新的自旋标记物与4-叠氮基-TEMPO，叠氮基苯丙氨酸和含叠氮基苯丙氨酸的蛋白质缀合。
• Synthesis of Next-Generation Maleimide Radical Labels
  作者：Janet Lovett、Bouchra Hajjaj、Anokhi Shah、Stacey Bell、Sally Shirran、Catherine Botting、Alexandra Slawin、Alison Hulme

  DOI：10.1055/s-0035-1562451

  日期：——

  The synthesis and characterization of four new nitroxide-radical-containing next-generation maleimides are presented. Each new label has a single leaving group which is either a phenoxyl or bromide. The linker between the maleimide and the nitroxide-containing framework is either a racemic mixture of a short chain or an achiral longer chain. These molecules have been designed to site-specifically label

  介绍了四种新的含氮氧自由基的下一代马来酰亚胺的合成和表征。每个新标签都有一个单独的离去基团，即苯氧基或溴化物。马来酰亚胺和含氮氧化合物骨架之间的接头是短链或非手性长链的外消旋混合物。这些分子已被设计为在用于磁共振研究的蛋白质中位点特异性地标记邻近半胱氨酸。最终产品的表征包括晶体学和抹香鲸肌红蛋白的标记。
• Synthesis and potential use of 1,8-naphthalimide type 1O2 sensor molecules
  作者：Tamás Kálai、Éva Hideg、Ferhan Ayaydin、Kálmán Hideg

  DOI：10.1039/c2pp25253h

  日期：2013.3

  New double (fluorescent and spin) sensor molecules containing 4-amino substituted 1,8-naphthalimide as a fluorophore and a sterically hindered amine (pre-nitroxide) or pyrroline nitroxide as a quencher and radical capturing moiety were synthesized. All sensors were substituted with a diethylaminoethyl sidechain to increase the water solubility. Steady state fluorescence properties of these compounds and their responses to ROS in vitro are reported with perspectives of plant physiology use in vivo.

  合成了新型双重（荧光和自旋）传感分子，这些分子以4-氨基取代的1,8-萘二酰亚胺作为荧光团，并以空间位阻的胺（前硝基氧化物）或吡咯啉硝基氧化物作为猝灭剂和自由基捕获基团。所有传感器均采用二乙氨基乙基侧链进行取代，以提高水溶性。报告了这些化合物的稳态荧光特性及其对体外活性氧（ROS）的反应，并探讨其在植物生理学中的体内应用前景。
• Combining benzo[d]isoselenazol-3-ones with sterically hindered alicyclic amines and nitroxides: enhanced activity as glutathione peroxidase mimics
  作者：Tamas Kálai、Govindasamy Mugesh、Gouriprasanna Roy、Helmut Sies、Zoltán Berente、Kálmán Hideg

  DOI：10.1039/b509865c

  日期：——

  Benzo[d]isoselenazol-3-ones N-substituted with sterically hindered diamagnetic and paramagnetic five- or six-membered nitroxides or their precursors, including ring-opened diselenides, exhibit synergism in glutathione peroxidase (GPx) activity.

  苯并[d]异硒唑-3-酮与立体受阻的二磁性和顺磁性五元或六元硝基化合物或其前体（包括开环二硒化物）进行 N-取代后，在谷胱甘肽过氧化物酶（GPx）活性方面表现出协同作用。
• Studies of Structure−Activity Relationship of Nitroxide Free Radicals and Their Precursors as Modifiers Against Oxidative Damage
  作者：Murali C. Krishna、William DeGraff、Olga H. Hankovszky、Cecília P. Sár、Tamás Kálai、József Jekő、Angelo Russo、James B. Mitchell、Kálmán Hideg

  DOI：10.1021/jm9802160

  日期：1998.8.1

  The protective effects of stable nitroxides, as well as their hydroxylamine and amine precursors, have been tested in Chinese hamster V79 cells subjected to H2O2 exposure at fixed concentration or exposure to ionizing radiation. Cytotoxicity was evaluated by monitoring the viability of the cells assessed by the clonogenic assay. The compounds tested at fixed concentration varied in terms of ring size, oxidation state, and ring substituents. Electrochemical studies were carried out to measure the redox midpoint potentials. The studies show that in the case of protection against H2O2 exposure, the protection was determined by the ring size, oxidation state, and redox midpoint potentials. In general the protection factors followed the order nitroxides > hydroxylamines > amines. Both the six-membered ring nitroxides and substituted five-membered ring nitroxides were efficient protectors. For six-membered ring nitroxides, the compounds exhibiting the lowest midpoint potentials exhibited maximal protection. In the case of X-radiation, nitroxides were the most protective though some hydroxylamines were also efficient. The amines were in some cases found to sensitize the toxicity of aerobic radiation exposure. The protection observed by the nitroxides was not dependent on the ring size. However, the ring substituents had significant influence on the protection. Compounds containing a basic side chain were found to provide enhanced protection. The results in this study suggest that these compounds are novel antioxidants which can provide cytoprotection in mammalian cells against diverse types of oxidative insult and identify structural determinants optimal for protection against individual types of damage.