2,5-Dihydro-2,2,5,5-tetramethyl-3-[(triethylammonio)methyl]pyrrole-1-oxyl bromide | 136908-10-6

• 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: 2,5-Dihydro-2,2,5,5-tetramethyl-3-[(triethylammonio)methyl]pyrrole-1-oxyl bromide
• CAS: 136908-10-6
• 化学式: Br*C₁₅H₃₀N₂O
• 分子量: 334.32
• InChiKey: GQYAQIORDMGVIO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.01
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl 、 三乙胺 以 丙酮 为溶剂， 反应 144.0h， 以66%的产率得到2,5-Dihydro-2,2,5,5-tetramethyl-3-[(triethylammonio)methyl]pyrrole-1-oxyl bromide
  参考文献：
  名称：

  Studies of Structure−Activity Relationship of Nitroxide Free Radicals and Their Precursors as Modifiers Against Oxidative Damage

  摘要：

  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.

  DOI：

  10.1021/jm9802160

文献信息

• Structure of reversed micelles in the cyclohexane/polyoxyethylene(4)nonylphenol/water system, as studied by the spin probe technique
  作者：H. Caldararu、Agneta Caragheorgheopol、M. Dimonie、D. Donescu、Ileana Dragutan、N. Marinescu

  DOI：10.1021/j100196a051

  日期：1992.8

  The cyclohexane/polyoxyethylene(4)nonylphenol (EO(4)NP)/water system (2.8% EO(4)NP) with [H2O]/[EO(4)NP] molar ratios between 0.1 and 6.9, has been investigated by electron spin resonance (ESR) spectroscopy using the following nitroxides: 3-carboxy-2,2,5,5-tetramethylpyrroline-1-oxyl (I), 2,5-dihydro-2,2,5,5-tetramethyl-3-[(triethylammonio)methyl]pyrrole-1-oxyl bromide (II), and 5-doxylstearic acid (IV) as spin probes. For radicals I and II the nitrogen hyperfine splitting, a(N), and the rotational correlation time, tau(c), have been analyzed, yielding information about the polarity and viscosity of their locations. At [H2O]/[EO(4)NP] less-than-or-equal-to 0.3, the presence of "waterless' micellar aggregates in fast exchange (nu(ex) > 10(6) s-1) with the monomer surfactant is evident. At [H2O]/[EO(4)NP] = 0.6, the core viscosity is at its maximum value and the exchange rate decreases below the limit of slow exchange (nu(ex) < 10(6) s-1). Upon further increasing the water content, the core becomes more polar and less viscous, with these parameters approaching their values in bulk water. The effect of Cu(II) ion (in an oil-soluble complex) on the spectra of radical II-confined to the water-pool-has been interpreted by using Leigh's theory, and the "distance of closest approach" between these two paramagnetic species has been evaluated. This distance is considered to represent a measure of the penetrability of the micellar shell. Radical IV yielded anisotropic spectra in the aggregates with slow exchange. From their ESR parameters the order degree of the surfactant chains in the micellar shell has been evaluated. All results are consistent, indicating reduced penetrability and increased order with increasing dimensions of the water-pool.
• 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.