4-吡啶甲醛,3-羟基-2-甲基-5-[(苯基甲氧基)甲基]- | 169689-24-1

• 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
• 中文名称: 4-吡啶甲醛,3-羟基-2-甲基-5-[(苯基甲氧基)甲基]-
• 英文名称: 5-(benzyloxymethyl)-3-hydroxy-2-methylpyridine-4-carbaldehyde
• 英文别名: 5-((Benzyloxy)methyl)-3-hydroxy-2-methylpyridine-4-carbaldehyde；3-hydroxy-2-methyl-5-(phenylmethoxymethyl)pyridine-4-carbaldehyde
• CAS: 169689-24-1
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: MPWMSAJNPIRBOY-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  441.9±40.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-吡啶甲醛,3-羟基-2-甲基-5-[(苯基甲氧基)甲基]- 在 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 5-(benzyloxymethyl)-3-(2-ethoxyethoxy)-2-methylpyridine-4-carbaldehyde
  参考文献：
  名称：

  通过新型吡哆醛模型化合物对α-氨基酸进行有效的α-烷基化

  摘要：

  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。

  DOI：

  10.1246/cl.1995.487
• 作为产物：
  描述：

  2-甲基-3-羟基-4,5-二羟甲基吡啶 在 manganese(IV) oxide 、 甲酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 氯仿 、 丙酮 为溶剂， 生成 4-吡啶甲醛,3-羟基-2-甲基-5-[(苯基甲氧基)甲基]-
  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

文献信息

• α-alkylation of α-amino esters by using a pyridoxal model compound having a Li+-ionophore character
  作者：Kazuyuki Miyashita、Hideto Miyabe、Chiaki Kurozumi、Kuninori Tai、Takeshi Imanishi

  DOI：10.1016/0040-4020(96)00704-1

  日期：1996.9

  Synthesis of α,α-dialkyl-α-amino esters by α-alkylation of aldimines prepared from a novel pyridoxal model compound was studied. The α-alkylation of the aldimines having an ethoxy-ethoxy group at C-3 proceeded most rapidly when LiOH was employed as a base and gave α,α-dialkyl-α-amino esters after acidic hydrolysis. The chelated structure composed of the aldimine and Li+ was also revealed by 1H-NMR analysis

  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。
• Substituted pyridoxines as anti-platelet agents
  申请人：Haque Wasimul

  公开号：US20060094749A1

  公开（公告）日：2006-05-04

  Compounds with antiplatelet aggregation characteristics for the treatment of cardiovascular and cardiovascular related disease, are described. The methods are directed to administering pharmaceutical compositions comprising a pyridoxine analogue.

  描述了具有抗血小板聚集特性的化合物，用于治疗心血管和心血管相关疾病。这些方法涉及使用含有吡哆醇类似物的药物组合物。
• Substituted Pyridoxines As Anti-Platelet Agents
  申请人：Haque Wasimul

  公开号：US20080306108A1

  公开（公告）日：2008-12-11

  Compounds with antiplatelet aggregation characteristics for the treatment of cardiovascular and cardiovascular related disease, are described. The methods are directed to administering pharmaceutical compositions comprising a pyridoxine analogue.

  本文描述了用于治疗心血管和心血管相关疾病的抗血小板聚集特性化合物。该方法涉及给予含有吡哆醇类似物的药物组合物。
• EP1824825A4
  申请人：——

  公开号：EP1824825A4

  公开（公告）日：2009-07-08
• SUBSTITUTED PYRIDOXINES AS ANTI-PLATELET AGENTS
  申请人：Medicure International Inc.

  公开号：EP1824825A1

  公开（公告）日：2007-08-29