6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether) | 582322-85-8

• 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)
• 英文别名: 6-Dimethylaminopyridoxine-a4-(tert-butyldimethylsilyl ether)；4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(dimethylamino)-5-(hydroxymethyl)-2-methylpyridin-3-ol
• CAS: 582322-85-8
• 化学式: C₁₆H₃₀N₂O₃Si
• 分子量: 326.511
• InChiKey: CKZCTDQYGVURQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl ether) 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 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：

  聚合甲醛 、 6-aminopyridoxine-α⁴-tert-butyldimethylsilyl ether 在 三乙酰氧基硼氢化钠 、 甲醇 、 sodium cyanoborohydride 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 42.17h， 以48%的产率得到6-dimethylaminopyridoxine-α⁴-(tert-butyldimethylsilyl 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).