5-(benzyloxy)-2-hydroxybenzaldehyde oxime | 1206675-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(benzyloxy)-2-hydroxybenzaldehyde oxime
• CAS: 1206675-07-1
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: KHLROCZVJVPTQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-2-hydroxybenzaldehyde oxime 在 盐酸 、 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Characterization of Scavengers of γ-Ketoaldehydes That Do Not Inhibit Prostaglandin Biosynthesis

  摘要：

  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.

  DOI：

  10.1021/tx900407a
• 作为产物：
  描述：

  4-苄氧基苯酚 在 盐酸羟胺 、 sodium acetate 、 三乙胺 、 magnesium chloride 作用下， 生成 5-(benzyloxy)-2-hydroxybenzaldehyde oxime
  参考文献：
  名称：

  Characterization of Scavengers of γ-Ketoaldehydes That Do Not Inhibit Prostaglandin Biosynthesis

  摘要：

  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.

  DOI：

  10.1021/tx900407a