6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether)-3,α⁵-di(methoxymethyl ether) | 582322-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether)-3,α⁵-di(methoxymethyl ether)
• 英文别名: 4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(methoxymethoxy)-3-(methoxymethoxymethyl)-N,N,6-trimethylpyridin-2-amine
• CAS: 582322-87-0
• 化学式: C₂₀H₃₈N₂O₅Si
• 分子量: 414.618
• InChiKey: HTYKTGWDLKEEGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  62.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether)-3,α⁵-di(methoxymethyl ether) 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到6-dimethylaminopyridoxine-3,α⁵-di(methoxymethyl ether)
  参考文献：
  名称：

  Synthesis of a Novel Radical Trapping and Carbonyl Group Trapping Anti-AGE Agent:  A Pyridoxamine Analogue for Inhibiting Advanced Glycation (AGE) and Lipoxidation (ALE) End Products

  摘要：

  [GRAPHICS]Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).

  DOI：

  10.1021/ol0348147
• 作为产物：
  描述：

  氯甲基甲基醚 、 6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether) 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether)-3,α⁵-di(methoxymethyl ether)
  参考文献：
  名称：

  Synthesis of a Novel Radical Trapping and Carbonyl Group Trapping Anti-AGE Agent:  A Pyridoxamine Analogue for Inhibiting Advanced Glycation (AGE) and Lipoxidation (ALE) End Products

  摘要：

  [GRAPHICS]Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).

  DOI：

  10.1021/ol0348147

文献信息

• Synthesis of a Novel Radical Trapping and Carbonyl Group Trapping Anti-AGE Agent:  A Pyridoxamine Analogue for Inhibiting Advanced Glycation (AGE) and Lipoxidation (ALE) End Products
  作者：Sean M. Culbertson、Gary D. Enright、K. U. Ingold

  DOI：10.1021/ol0348147

  日期：2003.7.1

  [GRAPHICS]Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).