2-<2-<2-furanylmethylthio>ethanamino>-5-<2-methoxypyrid-4-ylmethyl>-4-pyrimidone | 92838-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-<2-<2-furanylmethylthio>ethanamino>-5-<2-methoxypyrid-4-ylmethyl>-4-pyrimidone
• 英文别名: 2-[2-(furan-2-ylmethylsulfanyl)ethylamino]-5-[(2-methoxypyridin-4-yl)methyl]-1H-pyrimidin-6-one
• CAS: 92838-84-1
• 化学式: C₁₈H₂₀N₄O₃S
• 分子量: 372.448
• InChiKey: ARQYSGDCJSEYAH-UHFFFAOYSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-<2-<2-furanylmethylthio>ethanamino>-5-<2-methoxypyrid-4-ylmethyl>-4-pyrimidone 在 盐酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 18.0h， 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-氰基-2-甲氧基吡啶 在 palladium on activated charcoal 、 镍 哌啶 、 吡啶 、 盐酸 、 聚合甲醛 、 氢气 、 sodium methylate 、 盐酸氨基脲 、 sodium acetate 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 62.5h， 生成 2-<2-<2-furanylmethylthio>ethanamino>-5-<2-methoxypyrid-4-ylmethyl>-4-pyrimidone
  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

• Chemical process for preparing H2-antagonists
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0112637A2

  公开（公告）日：1984-07-04

  A chemical process is described for the preparation of H2-antagonists or precursors thereof, of the formula (V): wherein R' is 5-methylimidazol-4-yl, furan-2-yl or 5-dimeth- ylaminomethylfuran-2-yl and R2 is 3,4-methylenedioxyphenyl or optionally protected 2-hydroxypyrid-4-yl; which process comprises reacting a compound of the formula (VI) with a compound of the formula (VII): wherein R3 is C1-6alkyl; and thereafter if desired deprotecting a protected hydroxy group, converting a compound wherein R1 is furan-2-yl into a compound wherein R1 is 5-di- methylaminomethylfuran-2-yl, and/or forming a pharmaceutically acceptable salt.

  描述了一种制备式(V)的 H2-拮抗剂或其前体的化学工艺： 其中 R'为 5-甲基咪唑-4-基、呋喃-2-基或 5-二甲基氨基甲基呋喃-2-基，R2 为 3,4-亚甲基二氧苯基或经选择保护的 2-羟基吡啶-4-基；该工艺包括使式（VI）化合物与式（VII）化合物反应： 其中 R3 为 C1-6 烷基；然后，如果需要，对受保护的羟基进行脱保护，将 R1 为呋喃-2-基的化合物转化为 R1 为 5-二甲氨基甲基呋喃-2-基的化合物，和/或形成药学上可接受的盐。
• Chemical process
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0141560B1

  公开（公告）日：1989-01-25
• Isocytosine H2-receptor histamine antagonists. IV. The synthesis and biological activity of donetidine (SK&amp;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.