5'-O-benzylpyridoxine | 26864-21-1

• 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: 5'-O-benzylpyridoxine
• 英文别名: 4-(Hydroxymethyl)-2-methyl-5-(phenylmethoxymethyl)pyridin-3-ol
• CAS: 26864-21-1
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: QPFPUSKNIFCZMW-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  493.5±40.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-O-benzylpyridoxine 在 manganese(IV) oxide 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 63.0h， 生成 5-(benzyloxymethyl)-3-(2-ethoxyethoxy)-2-methylpyridine-4-carbaldehyde
  参考文献：
  名称：

  通过使用具有Li +-离子载体特性的吡ido醛模型化合物，对α-氨基酯进行α-烷基化

  摘要：

  研究了由新型吡ido醛模型化合物制得的亚胺的α-烷基化反应，合成α，α-二烷基-α-氨基酯。当使用LiOH作为碱并在酸性水解后得到α，α-二烷基-α-氨基酯时，在C-3处具有乙氧基-乙氧基的醛亚胺的α-烷基化进行得最快。通过1 H-NMR分析还揭示了由醛亚胺和Li +组成的螯合结构。

  DOI：

  10.1016/0040-4020(96)00704-1
• 作为产物：
  描述：

  2-甲基-3-羟基-4,5-二羟甲基吡啶 在 甲酸 、 sodium hydride 、 对甲苯磺酸 作用下， 生成 5'-O-benzylpyridoxine
  参考文献：
  名称：

  Shih, Younan; Yang, Ding-Yah; Weigel, Theresa M., Journal of the American Chemical Society, 1990, vol. 112, # 26, p. 9652 - 9654

  摘要：

  DOI：

文献信息

• Efficient<i>α</i>-Alkylation of<i>α</i>-Amino Acids by Means of a Novel Pyridoxal Model Compound
  作者：Kazuyuki Miyashita、Hideto Miyabe、Chiaki Kurozumi、Takeshi Imanishi

  DOI：10.1246/cl.1995.487

  日期：1995.6

  α-Alkyl-α-amino esters were prepared by the alkylation of α-imino esters obtained from α-amino acids and a novel PLP model compound possessing a Li+ ionophore character.

  α-烷基-α-氨基酯是通过从α-氨基酸和具有Li+离子载体特征的新型PLP模型化合物获得的α-亚氨基酯的烷基化制备的。
• Characterization of Scavengers of γ-Ketoaldehydes That Do Not Inhibit Prostaglandin Biosynthesis
  作者：Irene Zagol-Ikapitte、Venkataraman Amarnath、Manju Bala、L. Jackson Roberts、John A. Oates、Olivier Boutaud

  DOI：10.1021/tx900407a

  日期：2010.1.18

  Expression Of cyclooxygenase-2 (COX-2) is associated with the development of many pathologic conditions. The product of COX-2, prostaglandin H(2) (PGH(2)), can spontaneously rearrange to form reactive gamma-ketoaldehydes called levuglandins (LGs). This gamma-keloaldehyde structure confers a high degree of reactivity on the LGs, which rapidly form covalent adducts with primary amines of protein residues. Formation of LG adducts of proteins has been demonstrated in pathologic conditions (e.g., increased levels in the hippocampus in Alzheimer's disease) and during physiologic function (platelet activation). On the basis of knowledge that lipid modification of proteins is known to cause their translocation and to alter their function. we hypothesize that modification of proteins by LG could have functional consequences. Testing this hypothesis requires an experimental approach that discriminates between the effects of protein modification by LG and the, effects of cyclooxygenase-derived prostanoids acting through their G-protein Coupled receptors. TO achieve this goal, we have synthesized and evaluated it series of scavengers that react with LG with a potency More than 2 orders of magnitude greater than that with the epsilon-amine of lysine. A Subset of these scavengers are shown to block the formation of LG adducts of proteins in cells without inhibiting the catalytic activity of the cyclooxygenases. Ten of these selective scavengers did not produce cytotoxicity. These results demonstrate that small molecules can scavenge LGs in cells without interfering with the formation of prostaglandins. They also provide a working hypothesis for the development of pharmacologic agents that could be used in experimental animals in vivo to assess the pathophysiological contribution of levuglandins in diseases associated with cyclooxygenase up-regulation.
• Chemical synthesis of stereospecifically labeled pyridoxamine 5'-phosphate
  作者：Ding Yah Yang、Younan Shih、Hung Wen Liu

  DOI：10.1021/jo00008a071

  日期：1991.4
• YANG, DING-YAH;SHIH, YOUNAN;LIU, HUNG VEN, J. ORG. CHEM., 56,(1991) N, C. 2940-2946
  作者：YANG, DING-YAH、SHIH, YOUNAN、LIU, HUNG VEN

  DOI：——

  日期：——