(2,2,5,5-tetramethyl-1H-pyrrol-3-yl)methanol | 123665-64-5

• 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: (2,2,5,5-tetramethyl-1H-pyrrol-3-yl)methanol
• CAS: 123665-64-5
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: POPKJYLKEVTMAD-UHFFFAOYSA-N

物化性质

• 熔点：
  66-69 °C
• 沸点：
  229.3±20.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,2,5,5-tetramethyl-1H-pyrrol-3-yl)methanol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以89%的产率得到2,2,5,5-四甲基-2,5-二氢-1H-吡咯-3-甲醛
  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
• 作为产物：
  描述：

  四甲基哌啶酮 在 溴 、 sodium methylate 、 溶剂黄146 、 红铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (2,2,5,5-tetramethyl-1H-pyrrol-3-yl)methanol
  参考文献：
  名称：

  An efficient synthesis of 3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline, a promising radioprotector for cancer radiotherapy

  摘要：

  Nitroxides can ameliorate the toxic effects of radiation during cancer therapy. Nitroxides are paramagnetic and can be used in magnetic resonance imaging (MRI) and electron paramagnetic resonance imaging (EPRI) to monitor in vivo oxidative stress status. Compound 5 (3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline) was found to be the most effective nitroxide radioprotector. An efficient synthesis for this promising radioprotector was developed. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.08.028

文献信息

• Improvement of a Critical Intermediate Step in the Synthesis of a Nitroxide-Based Spin-Labeled Deoxythymidine Analog
  作者：Jeannine Powell、Edward Johnson、Peter Gannett

  DOI：10.3390/51201244

  日期：——

  Rozantsev [3]; further elaboration of these compounds is described in severalsources [2,4]. In our hands, one of the most problematic steps in the overall synthesis is the reductionof the carboxylic acid moiety in 1 to the alcohol 2, which is then oxidized to the aldehyde 3, withoutperturbation of the nitroxide (Figure 1).Here we report several methods we have utilized for theconversion of 1 into 2 and in

  Jeannine H. Powell、Edward M. Johnson II 和 Peter M. Gannett*西弗吉尼亚大学药学院基础药物科学系，邮政信箱 9530，美国西弗吉尼亚州摩根敦。电话。(304)-293-1480，传真 [phone]。*通讯作者；电子邮件 [e-mail] 收到：2000 年 5 月 8 日；2000 年 11 月 13 日修订/接受：2000 年 11 月 14 日/出版：2000 年 12 月 18 日摘要：将 3-羧基-2,2,5,5-四甲基-吡咯啉-1-氧基中的羧酸部分还原为醇的方法已经探索了相应醛的中间体并开发了一种改进的方法。关键词：氮氧化物，自旋标记，还原，羧酸，醇，酸酐引言自旋标记的核酸已被提议作为 DNA 构象和动力学研究的探针 [1, 2]。一个潜在的非常有用的部分是胸苷类似物，它通过乙炔桥与吡咯啉-N-氧基分子偶联
• [EN] COMPOSITIONS AND METHODS FOR INHIBITION OF CANCERS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR L'INHIBITION DE CANCERS
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2011005790A1

  公开（公告）日：2011-01-13

  Methods and compositions for treating cancers, including ovarian cancers, are described. The compositions generally include a redox based curcumin derivative, diarylidenylpiperiden-4-one (DAP) having a hydroxylamine moiety attached thereto.

  描述了用于治疗癌症的方法和组合物，包括卵巢癌。这些组合物通常包括一种基于氧化还原的姜黄素衍生物，即联苯亚基哌啶-4-酮（DAP），其上附有一个羟胺基团。
• COMPOSITIONS AND METHODS FOR INHIBITION OF CANCERS
  申请人：The Ohio State University Research Foundation

  公开号：EP2451273A1

  公开（公告）日：2012-05-16
• An efficient synthesis of 3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline, a promising radioprotector for cancer radiotherapy
  作者：Haitao Wu、Vincent Coble、Olga Vasalatiy、Rolf E. Swenson、Murali C. Krishna、James B. Mitchell

  DOI：10.1016/j.tetlet.2014.08.028

  日期：2014.10

  Nitroxides can ameliorate the toxic effects of radiation during cancer therapy. Nitroxides are paramagnetic and can be used in magnetic resonance imaging (MRI) and electron paramagnetic resonance imaging (EPRI) to monitor in vivo oxidative stress status. Compound 5 (3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline) was found to be the most effective nitroxide radioprotector. An efficient synthesis for this promising radioprotector was developed. Published by Elsevier Ltd.
• 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.