2-chloro-5-benzyloxy-pyrimidine | 1146543-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-5-benzyloxy-pyrimidine
• 英文别名: 2-chloro-5-(benzyloxy)-4,6-dimethoxypyrimidine；2-Chloro-4,6-dimethoxy-5-phenylmethoxypyrimidine
• CAS: 1146543-77-2
• 化学式: C₁₃H₁₃ClN₂O₃
• 分子量: 280.711
• InChiKey: JNKPVZLCNJBOAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-5-benzyloxy-pyrimidine 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 mineral oil 为溶剂， 生成 5-hydroxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine
  参考文献：
  名称：

  NEUROPROTECTIVE MULTIFUNCTIONAL ANTIOXIDANTS AND THEIR MONOFUNCTIONAL ANALOGS

  摘要：

  神经保护多功能抗氧化剂是含有2-二乙酰氨基-5-羟基嘧啶基团的化合物，具有以下结构式： 其中R1为CH2或C2H4；R2为H或—OR4，其中R4为H或芳基；R3a和R3b分别独立地选自H和—O-烷基的组。这些抗氧化剂是口服可利用的金属减弱多功能抗氧化剂，可以独立减弱过渡金属，以及清除自由基。由于这些多功能抗氧化剂化合物具有独立螯合金属（如Fe、Cu或Zn）和清除来自不同来源产生的自由基的能力，它们具有神经保护作用，并有助于治疗各种神经系统疾病，如阿尔茨海默病、帕金森病、肌萎缩侧索硬化症、创伤性脑损伤、眼部疾病（如白内障、青光眼、老年性黄斑变性和其他视网膜变性），以及减缓糖尿病并发症的进展。

  公开号：

  US20140235858A1
• 作为产物：
  描述：

  2-chloro-5-hydroxy-4,6-dimethoxypyrimidine 、 溴甲苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以85%的产率得到2-chloro-5-benzyloxy-pyrimidine
  参考文献：
  名称：

  Multifunctional Compounds and Methods of Use Thereof

  摘要：

  提供了包含多功能剂的组合物和使用方法。

  公开号：

  US20090105269A1

文献信息

• Orally Bioavailable Metal Chelators and Radical Scavengers: Multifunctional Antioxidants for the Coadjutant Treatment of Neurodegenerative Diseases
  作者：Hiroyoshi Kawada、Peter F. Kador

  DOI：10.1021/acs.jmedchem.5b00272

  日期：2015.11.25

  Neurodegenerative diseases are associated with oxidative stress that is induced by the presence of reactive oxygen species and the abnormal cellular accumulation of transition metals. Here, a new series of orally bioavailable multifunctional antioxidants (MFAO-2s) possessing a 2-diacetylamino-5-hydroxypyrimidine moiety is described. These MFAO-2s demonstrate both free radical and metal attenuating properties that are similar to the original published MFAO-1s that are based on 1-N,N'-dimethylsulfamoyl-1-4-(2-pyrimidyl)piperazine. Oral bioavailability studies in C57BL/6 mice demonstrate that the MFAO-2s accumulate in the brain at significantly higher levels than the MFAO-1s while achieving similar neural retina levels. The MFAO-2s protect human neuroblastoma and retinal pigmented epithelial cells against hydroxyl radicals in a dose-dependent manner by maintaining cell viability and intracellular glutathione levels. The MFAO-2s outperform clioquinol, a metal attenuator that has been investigated for the treatment of Alzheimer's disease.
• Multifunctional Antioxidants for the Treatment of Age-Related Diseases
  作者：Hongxia Jin、James Randazzo、Peng Zhang、Peter F. Kador

  DOI：10.1021/jm901381j

  日期：2010.2.11

  Analogues of N,N-dimethyl-4-(pyrimidin-2-yl)piperazine-l-sulfonamide possessing a free radical scavenger group (FRS), chelating groups (CHL), or both (FRS + CHL) have been synthesized. Electrospray ionization mass spectrometry studies indicate that select members of this series bind ions in the relative order of Cu1+ = Cu2+ >Fe2+ = Fe3+ > Zn2+ with no binding of Ca2+ or Mg2+ observed. In vitro evaluation of these compounds in human lens epithelial, human retinal pigmented epithelial, and human hippocampal astrocyte cell lines indicates that all analogues possessing the FRS group as well as the water-soluble vitamin E analogue 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid protect these cells against decreased cell viability and glutathione levels induced by hydrogen peroxide. In addition, those compounds possessing CHL groups also protected these cells against hydroxyl radicals generated by the Fenton reaction. These compounds are good candidates for the preventive treatment of cataract, age-related macular degeneration (AMD), and Alzheimer's dementia (AD).