2-nitroamino-5-(2-methoxy-pyridin-4-yl)methyl-4-pyrimidone | 72716-89-3

• 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-nitroamino-5-(2-methoxy-pyridin-4-yl)methyl-4-pyrimidone
• 英文别名: 2-nitroamino-5-(2-methoxypyrid-4-ylmethyl)-4-pyrimidone；2-nitroamino-5-(2-methoxy-pyridin-4-ylmethyl)-4-pyrimidone；2-nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone；2-nitroamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone；N-[5-[(2-methoxypyridin-4-yl)methyl]-6-oxo-1H-pyrimidin-2-yl]nitramide
• CAS: 72716-89-3
• 化学式: C₁₁H₁₁N₅O₄
• 分子量: 277.239
• InChiKey: DYSDJZQYNYDJBU-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195.5 °C
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-nitroamino-5-(2-methoxy-pyridin-4-yl)methyl-4-pyrimidone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 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 38.5h， 生成 2-nitroamino-5-(2-methoxy-pyridin-4-yl)methyl-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

• Intermediates in the process for making histamine antagonists
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04227000A1

  公开（公告）日：1980-10-07

  A process for making substituted 2-aminopyrimidones which are histamine H.sub.2 - antagonists which comprises reacting a 2-nitroaminopyrimidone with a heteroarylalkylamine, heteroarylalkylthioalkylamine, or heteroarylalkoxyalkylamine. One particular compound which can be made by this process is 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-[5-(1,3-benzodioxolyl) methyl]-4-pyrimidone. Also claimed are 2-nitroaminopyrimidone intermediates for use in this process. One specific intermediate is 2-nitroamino-5-[5-(1,3-benzodioxolyl)methyl]-4-pyrimidone.

  一种制备取代2-氨基嘧啶酮的方法，这些化合物是组胺H.sub.2-拮抗剂，包括将2-硝基氨基嘧啶酮与杂环烷基胺、杂环烷基硫代烷基胺或杂环烷基氧代烷基胺反应。通过这种方法可以制备一种特定化合物，即2-[2-(5-甲基-4-咪唑基甲硫基)乙基氨基]-5-[5-(1,3-苯并二氧杂环己基)甲基]-4-嘧啶酮。此外，还声明了用于该方法的2-硝基氨基嘧啶酮中间体。其中一个特定的中间体是2-硝基氨基-5-[5-(1,3-苯并二氧杂环己基)甲基]-4-嘧啶酮。
• Pyrimidone derivatives
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04385058A1

  公开（公告）日：1983-05-24

  This invention relates to 2-amino-4-pyrimidone derivatives, in which the amino group is substituted by a methylthioethyl, butyl or oxypropyl group bearing a terminal 4-dialkylaminomethyl-2-pyridyl group. The compounds have histamine H.sub.2 -antagonist activity. A specific compound of this invention is 2-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-5-(6-methyl-3- pyridylmethyl)-4-pyrimidone.

  这项发明涉及2-氨基-4-嘧啶酮衍生物，其中氨基团被甲硫乙基、丁基或氧丙基取代，带有一个末端的4-二烷基氨甲基-2-吡啶基团。这些化合物具有组胺H.sub.2-拮抗活性。该发明的一个具体化合物是2-[2-(4-二甲基氨甲基-2-吡啶基硫代)乙基氨基]-5-(6-甲基-3-吡啶基甲基)-4-嘧啶酮。
• 5-(Hydroxypyridylalkyl)-4-pyrimidones
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04255428A1

  公开（公告）日：1981-03-10

  The compounds are substituted 2-amino-4-pyrimidones with a 5-(hydroxypyridylalkyl) substituent which are histamine H.sub.2 -antagonists. Two specific compounds are 2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]-5-(2-hydroxy-4-pyridylmethyl )-4-pyrimidone and 2-[4-(3-methoxy-2-pyridyl)butylamino]-5-(2-hydroxy-4-pyridylmethyl)-4-pyri midone.

  这些化合物是具有5-(羟基吡啶基)取代基的2-氨基-4-嘧啶酮，是组胺H.sub.2-拮抗剂。两种特定的化合物是2-[2-(3-溴-2-吡啶甲硫基)乙基氨基]-5-(2-羟基-4-吡啶甲基)-4-嘧啶酮和2-[4-(3-甲氧基-2-吡啶基)丁基氨基]-5-(2-羟基-4-吡啶甲基)-4-嘧啶酮。
• 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。
• Pyridines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04439609A1

  公开（公告）日：1984-03-27

  This invention relates to 4-substituted aminomethyl pyridines with a butanamine, oxypropioamine or thiomethylamine substituent at the 2 position. The compounds are reacted with pyridones to form compounds which have histamine H.sub.2 -antagonist activity.

  本发明涉及在2位具有丁胺基、氧丙胺基或硫甲基取代基的4-取代氨基甲基吡啶中。这些化合物与吡啶酮反应形成具有组胺H.sub.2 -拮抗活性的化合物。