1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine | 342899-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine
• 英文别名: CMH；1-Hydroxy-2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid methyl ester；methyl 1-hydroxy-2,2,5,5-tetramethylpyrrolidine-3-carboxylate
• CAS: 342899-45-0
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: VPKKKPWJDYOHLC-UHFFFAOYSA-N

物化性质

• 沸点：
  257.1±29.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine 在 二乙烯三胺五醋酸 、 sodium chloride 、 xanthine oxidase 、 黄嘌呤 作用下， 生成 2,2,5,5-tetramethylpyrrolidine-1-oxyl-3-carboxylic acid methyl ester
  参考文献：
  名称：

  EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines

  摘要：

  Superoxide (O(2)(center dot-)) has been implicated in the pathogenesis of many human diseases, but detection of the O(2)(center dot-) radicals in biological systems is limited due to inefficiency of O(2)(center dot-) spin trapping and lack of site-specific information. This work studied production of extracellular, intracellular and mitochondrial O(2)(center dot-) in neutrophils, cultured endothelial cells and isolated mitochondria using a new set of cationic, anionic and neutral hydroxylamine spin probes with various lipophilicity and cell permeability. Cyclic hydroxylamines rapidly react with O(2)(center dot-), producing stable nitroxides and allowing site-specific O(2)(center dot-) detection in intracellular, extracellular and mitochondrial compartments. Negatively charged 1-hydroxy-4-phosphono-oxy-2,2,6, 6-tetramethylpiperidine (PP-H) and positively charged 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl-trimethylammonium (CAT1-H) detected only extramitochondrial O(2)(center dot-). Inhibition of EPR signal by SOD2 over-expression showed that mitochondria targeted mitoTEMPO-H detected intramitochondrial O(2)(center dot-) both in isolated mitochondria and intact cells. Both 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine (CP-H) and 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (CM-H) detected an increase in cytoplasm O(2)(center dot-) stimulated by PMA, but only CM-H and mitoTEMPO-H showed an increase in rotenone-induced mitochondrial O(2)(center dot-). These data show that a new set of hydroxylamine spin probes provide unique information about site-specific production of the O(2)(center dot-) radical in extracellular or intracellular compartments, cytoplasm or mitochondria.

  DOI：

  10.3109/10715762.2010.540242
• 作为产物：
  描述：

  3-羧基-PROXYL 在 盐酸 、 肼 作用下， 以 甲醇 为溶剂， 反应 18.5h， 生成 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine
  参考文献：
  名称：

  Acyl-Protected Hydroxylamines as Spin Label Generators for EPR Brain Imaging

  摘要：

  In a search for novel electron paramagnetic resonance (EPR) brain imaging agents, we have designed and synthesized the acyl-protected hydroxylamines 1-acetoxy-4-methoxycarbonyl-2,2,6,6-tetramethylpiperidine (AMCPe), 1-acetoxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (AMCPy), and 1-acetoxy-3-(acetoxymethoxy)carbonyl-2,2,5,5-tetramethylpyrrolidine (DACPy), in which both the ring size and the number of ester functions were varied. In all of them, the nitroxide was first reduced and the resultant hydroxylamine was then protected with an acetyl group. These compounds are lipophilic, which is a major prerequisite for blood-brain barrier penetration. Once in the brain, esterases and oxidants quickly convert these derivatives into ionic, water-soluble radicals and thus EPR detectable species that then reside in the central nervous system for periods of time sufficient for detection and imaging. The biological relevancy of these new compounds in mice has been assessed, and their biodistribution patterns have been compared. The five-membered ring derivative AMCPy emerged as a potent EPR brain imaging agent while the other two derivatives, AMCPe and DACPy, were quite ineffective.

  DOI：

  10.1021/jm0105169
• 作为试剂：
  描述：

  2-butyl-3-hydroxy-4(1H)-quinoline 在 HodC-W₁₆₀A protein, HodC: 1H-3-hydroxy-4-oxoquinaldine 2,4-dioxygenase C₆₉S mutant 、 三苯基膦 、 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine 作用下， 生成 2-butyl-2-hydroxy-1,2-dihydroquinoline-3,4-dione 、 3-hydroxy-2-butyl-4(1H)-quinolone
  参考文献：
  名称：

  Substrate-Assisted O2 Activation in a Cofactor-Independent Dioxygenase

  摘要：

  In contrast to the majority of O-2-activating enzymes, which depend on an organic cofactor or a metal ion for catalysis, a particular group of structurally unrelated oxygenases is functional without any cofactor. In this study, we characterized the mechanism of O-2 activation in the reaction pathway of a cofactor-independent dioxygenase with an alpha/beta-hydrolase fold, which catalyzes the oxygenolytic cleavage of 2-alkyl-3-hydroxy-4(1H)-quinolones. Chemical analysis and electron paramagnetic resonance spectroscopic data revealed that O-2 activation in the enzyme's active site is substrate-assisted, relying on single electron transfer from the bound substrate anion to Ow(2) to form a radical pair, which recombines to a C2-peroxide intermediate. Thus, an oxygenase can function without a cofactor, if the organic substrate itself, after activation to a (carb) anion by an active-site base, is intrinsically reactive toward molecular oxygen.

  DOI：

  10.1016/j.chembiol.2013.11.013

文献信息

• Process for producing oxide with higher oxidation than alcohol
  申请人：——

  公开号：US20030114712A1

  公开（公告）日：2003-06-19

  The present invention provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound thereon and an oxidative catalyst thereon, and oxidizing the alcohol compound in the presence of an oxidizing agent, giving an oxide higher in oxidizing degree than the alcohol compound, and also provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound, and subjecting the alcohol compound to an electrolytic oxidation, giving an oxide higher in oxidizing degree than the alcohol compound.

  本发明提供了一种从醇类化合物制备氧化物的方法，该方法包括以下步骤：使二氧化硅胶携带该醇类化合物和氧化催化剂，并在氧化剂存在下氧化该醇类化合物，得到比醇类化合物氧化程度更高的氧化物；同时还提供了一种从醇类化合物制备氧化物的方法，该方法包括以下步骤：使二氧化硅胶携带该醇类化合物，并将该醇类化合物进行电解氧化，得到比醇类化合物氧化程度更高的氧化物。
• MITOCHONDRIA TARGETED CATIONIC ANTI-OXIDANT COMPOUNDS FOR PREVENTION, THERAPY OR TREATMENT OF HYPER-PROLIFERATIVE DISEASE, NEOPLASIAS AND CANCERS
  申请人：Zarling David A.

  公开号：US20110059922A1

  公开（公告）日：2011-03-10

  The inventions disclosed include methods of treating cancers and related neoplasias, especially prostate cancer, with pharmaceutically acceptable salts comprising lipophilic cation moieties linked to nitroxide or linked to hydroxylamine anti-oxidant groups.

  披露的发明包括使用含有脂溶性阳离子基团与亚硝酰基或羟胺抗氧化基团相连的药用盐来治疗癌症和相关的新生物病变，特别是前列腺癌的方法。
• Processes for producing oxide with higher oxidation than alcohol
  申请人：Tanaka Hideo

  公开号：US20050014957A1

  公开（公告）日：2005-01-20

  The present invention provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound thereon and an oxidative catalyst thereon, and oxidizing the alcohol compound in the presence of an oxidizing agent, giving an oxide higher in oxidizing degree than the alcohol compound, and also provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound, and subjecting the alcohol compound to an electrolytic oxidation, giving an oxide higher in oxidizing degree than the alcohol compound.

  本发明提供了一种从醇类化合物生产氧化物的方法，该方法包括以下步骤：使二氧化硅凝胶携带醇类化合物和氧化催化剂，然后在氧化剂存在下将醇类化合物氧化，得到比醇类化合物氧化度更高的氧化物。同时，本发明还提供了一种从醇类化合物生产氧化物的方法，该方法包括以下步骤：使二氧化硅凝胶携带醇类化合物，然后对该醇类化合物进行电解氧化，得到比醇类化合物氧化度更高的氧化物。
• 6-HYDROXY-2-NAPHTHYLCARBINOL AND PROCESS FOR THE PREPARATION THEREOF
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1186588A1

  公开（公告）日：2002-03-13

  6-Hydroxy-2-naphthylcarbinol useful as a synthetic intermediate for preparation of 6-hydroxy-2-naphthaldehyde represented by the following formula (I), and a method for preparing 6-hydroxy-2-naphthylcarbinol comprising the step of reducing 6-hydroxy-2-naphthalenecarboxylic acid.

  6- 羟基-2-萘甲醇，可用作制备下式 (I) 所代表的 6- 羟基-2-萘甲醛的合成中间体，以及制备 6- 羟基-2-萘甲醇的方法，包括还原 6- 羟基-2-萘甲酸的步骤。
• Methods for treatment of vascular endothelial dysfunction using nicotinamide mononucleotide
  申请人：The Regents of the University of Colorado, a Body Corporate

  公开号：US10307437B2

  公开（公告）日：2019-06-04

  This invention is about the compositions and methods for assessing and treating vascular endothelial dysfunction. Various aspects provide a method for treatment of vascular endothelial dysfunction, comprising administering a composition comprising nicotinamide mononucleotide and a pharmaceutical excipient to a subject. In one embodiment the dose is administered to subjects in response to the indicator. In another embodiment the dose is administered chronically to subjects.

  本发明是关于评估和治疗血管内皮功能障碍的组合物和方法。各方面提供了一种治疗血管内皮功能障碍的方法，包括向受试者施用包含烟酰胺单核苷酸和药用赋形剂的组合物。在一个实施方案中，根据指标向受试者施用剂量。在另一个实施方案中，对受试者长期给药。