Ethyl 2-formyl-3-(4-methoxypyridin-2-yl)propanoate | 72830-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2-formyl-3-(4-methoxypyridin-2-yl)propanoate
• 英文别名: ethyl 2-formyl-3-(4-methoxypyridin-2-yl)propanoate
• CAS: 72830-11-6
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: WRMUVBMRAHLCHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-formyl-3-(4-methoxypyridin-2-yl)propanoate 在 氢溴酸 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 62.0h， 生成
  参考文献：
  名称：

  Isocytosine H2-receptor histamine antagonists. IV. The synthesis and biological activity of donetidine (SK&F 93574) and related compounds

  摘要：

  The synthesis and biological activity of some novel 2-amino-4-pyrimidone derivatives is described. Side-chains associated with H-2-antagonist activity am attached through the 2-amino group, whilst a range of 2-hydroxypyridine containing moieties are substituted at the 5-position of the pyrimidone ring. Good H-2-receptor histamine antagonist activity is observed with all the series and the majority of the compounds are selective for the H-2-receptor. High aqueous solubility and iv potency coupled with an extended duration of biological activity in animal models led to compound 16c, 2-[2-(5-dimethylaminomethyl-2-furanylmethyl-thio)ethylamino]-5-(2-hydroxypyrid-4-ylmethyl)-4-pyrimidone (donetidine, SK&F 93574) being selected for clinical investigation as a potential parenterally administered therapeutic agent.

  DOI：

  10.1016/0223-5234(93)90091-r
• 作为产物：
  描述：

  4-甲氧基吡啶-2-醛 在 palladium on activated charcoal 哌啶 、 吡啶 、 氢气 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 20.0h， 生成 Ethyl 2-formyl-3-(4-methoxypyridin-2-yl)propanoate
  参考文献：
  名称：

  Isocytosine H2-receptor histamine antagonists. IV. The synthesis and biological activity of donetidine (SK&F 93574) and related compounds

  摘要：

  The synthesis and biological activity of some novel 2-amino-4-pyrimidone derivatives is described. Side-chains associated with H-2-antagonist activity am attached through the 2-amino group, whilst a range of 2-hydroxypyridine containing moieties are substituted at the 5-position of the pyrimidone ring. Good H-2-receptor histamine antagonist activity is observed with all the series and the majority of the compounds are selective for the H-2-receptor. High aqueous solubility and iv potency coupled with an extended duration of biological activity in animal models led to compound 16c, 2-[2-(5-dimethylaminomethyl-2-furanylmethyl-thio)ethylamino]-5-(2-hydroxypyrid-4-ylmethyl)-4-pyrimidone (donetidine, SK&F 93574) being selected for clinical investigation as a potential parenterally administered therapeutic agent.

  DOI：

  10.1016/0223-5234(93)90091-r

文献信息

• 2-nitro aminopyrimidone derivatives, a process for their preparation and their use to prepare 2-aminopyrimidone derivatives which have histamine H2-antagonist activity
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0004793B1

  公开（公告）日：1981-12-30
• Isocytosine H2-receptor histamine antagonists. IV. The synthesis and biological activity of donetidine (SK&F 93574) and related compounds
  作者：TH Brown、RC Blakemore、GJ Durant、CR Ganellin、ME Parsons、AC Rasmussen、DA Rawlings

  DOI：10.1016/0223-5234(93)90091-r

  日期：1993.1

  The synthesis and biological activity of some novel 2-amino-4-pyrimidone derivatives is described. Side-chains associated with H-2-antagonist activity am attached through the 2-amino group, whilst a range of 2-hydroxypyridine containing moieties are substituted at the 5-position of the pyrimidone ring. Good H-2-receptor histamine antagonist activity is observed with all the series and the majority of the compounds are selective for the H-2-receptor. High aqueous solubility and iv potency coupled with an extended duration of biological activity in animal models led to compound 16c, 2-[2-(5-dimethylaminomethyl-2-furanylmethyl-thio)ethylamino]-5-(2-hydroxypyrid-4-ylmethyl)-4-pyrimidone (donetidine, SK&F 93574) being selected for clinical investigation as a potential parenterally administered therapeutic agent.