4-[2-[5-(羟甲基)吡啶-2-基]乙氧基]苯甲醛 | 184766-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[2-[5-(羟甲基)吡啶-2-基]乙氧基]苯甲醛
• 英文名称: Benzaldehyde, 4-[2-[5-(hydroxymethyl)-2-pyridinyl]ethoxy]-
• 英文别名: 4-[2-[5-(hydroxymethyl)pyridin-2-yl]ethoxy]benzaldehyde
• CAS: 184766-83-4
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: UWWWQRBADGUDOV-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  483.8±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 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-[2-[5-(羟甲基)吡啶-2-基]乙氧基]苯甲醛 在 氯化亚砜 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-[6-[2-(4-Formylphenoxy)ethyl]pyridin-3-yl]acetonitrile
  参考文献：
  名称：

  Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone

  摘要：

  Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible; clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in, vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).

  DOI：

  10.1021/jm9605694
• 作为产物：
  描述：

  6-甲基烟酸甲酯 在 盐酸 、 lithium aluminium tetrahydride 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 26.5h， 生成 4-[2-[5-(羟甲基)吡啶-2-基]乙氧基]苯甲醛
  参考文献：
  名称：

  Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone

  摘要：

  Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible; clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in, vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).

  DOI：

  10.1021/jm9605694