2-[2-(5-dimethylaminomethyl-furan-2-ylmethylthio)ethylamino]-5-(6-methoxy-pyridin-3-ylmethyl)-4-pyrimidone | 153901-89-4

• 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-(5-dimethylaminomethyl-furan-2-ylmethylthio)ethylamino]-5-(6-methoxy-pyridin-3-ylmethyl)-4-pyrimidone
• 英文别名: 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone；2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-5-[(6-methoxypyridin-3-yl)methyl]-1H-pyrimidin-6-one
• CAS: 153901-89-4
• 化学式: C₂₁H₂₇N₅O₃S
• 分子量: 429.543
• InChiKey: XAOVISHZZQXURC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-(5-dimethylaminomethyl-furan-2-ylmethylthio)ethylamino]-5-(6-methoxy-pyridin-3-ylmethyl)-4-pyrimidone 在 盐酸 作用下， 以 乙醇 为溶剂， 以81%的产率得到2-[2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethylamino]-5-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-1H-pyrimidin-4-one; hydrochloride
  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：

  6-甲氧基烟腈 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 62.25h， 生成 2-[2-(5-dimethylaminomethyl-furan-2-ylmethylthio)ethylamino]-5-(6-methoxy-pyridin-3-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

• Pyrimidine compounds
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04234588A1

  公开（公告）日：1980-11-18

  The compounds are substituted pyrimidine compounds which are histamine H.sub.2 -antagonists. A specific compound of the present invention is 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(3-pyridylmet hyl)-4-pyrimidone.

  这些化合物是被取代的嘧啶化合物，它们是组胺H.sub.2-拮抗剂。本发明的一种特定化合物是2-[2-(5-二甲胺甲基)-2-呋喃甲硫基)乙基氨基]-5-(3-吡啶甲基)-4-嘧啶酮。
• Pyrimidones, processes for their preparation and pharmaceutical compositions containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0003677A2

  公开（公告）日：1979-08-22

  Pyrimidones which are histamine H2-antagonists have the structure in which D is hydrogen or an aminoalkyl group, X is oxygen or sulphur, Y is oxygen, sulphur or methylene, n is 2 or 3, Z is hydrogen or lower alkyl, A is Ci-C5 alkylene in which one methylene group can be replaced by oxygen or sulphur, and B is hydrogen, methyl, C3-C6 cycloalkyl, or an aryl or heteroaryl group.

  组胺 H2-拮抗剂嘧啶酮的结构如下 其中 D 是氢或氨基烷基，X 是氧或硫，Y 是氧、硫或亚甲基，n 是 2 或 3，Z 是氢或低级烷基，A 是 Ci-C5 亚烷基，其中一个亚甲基可被氧或硫取代，B 是氢、甲基、C3-C6 环烷基或芳基或杂芳基。
• US4234588A
  申请人：——

  公开号：US4234588A

  公开（公告）日：1980-11-18
• US4539207A
  申请人：——

  公开号：US4539207A

  公开（公告）日：1985-09-03
• US4649141A
  申请人：——

  公开号：US4649141A

  公开（公告）日：1987-03-10