2-Amino-4,6-dihydroxy-5-methoxy-pyrimidin | 98142-98-4

• 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-Amino-4,6-dihydroxy-5-methoxy-pyrimidin
• 英文别名: 2-amino-5-methoxypyrimidine-4,6-diol；2-amino-5-methoxy-1H-pyrimidine-4,6-dione；2-amino-4-hydroxy-5-methoxy-1H-pyrimidin-6-one
• CAS: 98142-98-4
• 化学式: C₅H₇N₃O₃
• 分子量: 157.129
• InChiKey: BEBIJDKTTZMGDN-UHFFFAOYSA-N

物化性质

• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Amino-4,6-dihydroxy-5-methoxy-pyrimidin 在 五氯化磷 、 苄基三乙基氯化铵 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以48%的产率得到4,6-dichloro-5-methoxypyrimidin-2-amine
  参考文献：
  名称：

  Structure−Activity Studies on a Series of a 2-Aminopyrimidine-Containing Histamine H₄ Receptor Ligands

  摘要：

  A series of 2-aminopyrimidines was synthesized as ligands of the histamine H-4 receptor (H4R). Working in part from a pyrimidine hit that was identified in an HTS campaign, SAR studies were carried out to optimize the potency, which led to compound 3,4-tert-butyl-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylamine. We further studied this compound by systematically modifying the core pyrimidine moiety, the methylpiperazine at position 4, the NH2 at position 2, and positions 5 and 6 of the pyrimidine ring. The pyrimidine 6 position benefited the most from this optimization, especially in analogs in which the 6-tert-butyl was replaced with aromatic and secondary amine moieties. The highlight of the optimization campaign was compound 4, 4-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzonitrile, which was potent in vitro and was active as an anti-inflammatory agent in an animal model and had antinociceptive activity in a pain model, which supports the potential of H4R antagonists in pain.

  DOI：

  10.1021/jm8005959
• 作为产物：
  描述：

  甲氧基马来酸二甲酯 、 碳酸胍 在 乙醇 、 sodium 作用下， 反应 2.5h， 以100%的产率得到2-Amino-4,6-dihydroxy-5-methoxy-pyrimidin
  参考文献：
  名称：

  Structure−Activity Studies on a Series of a 2-Aminopyrimidine-Containing Histamine H₄ Receptor Ligands

  摘要：

  A series of 2-aminopyrimidines was synthesized as ligands of the histamine H-4 receptor (H4R). Working in part from a pyrimidine hit that was identified in an HTS campaign, SAR studies were carried out to optimize the potency, which led to compound 3,4-tert-butyl-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylamine. We further studied this compound by systematically modifying the core pyrimidine moiety, the methylpiperazine at position 4, the NH2 at position 2, and positions 5 and 6 of the pyrimidine ring. The pyrimidine 6 position benefited the most from this optimization, especially in analogs in which the 6-tert-butyl was replaced with aromatic and secondary amine moieties. The highlight of the optimization campaign was compound 4, 4-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzonitrile, which was potent in vitro and was active as an anti-inflammatory agent in an animal model and had antinociceptive activity in a pain model, which supports the potential of H4R antagonists in pain.

  DOI：

  10.1021/jm8005959

文献信息

• Pyrazole derivatives and salts thereof
  申请人：Daiichi Pharmaceuticals Co., Ltd.

  公开号：US06573377B1

  公开（公告）日：2003-06-03

  This invention provides compounds having antitumor effect, namely a compound represented by the following formula (I) or (Ia) having various substituents in which G and G1 are condensed tricyclic heterocyclic rings or salts thereof, and a compound represented by the following formula (Ib) having various substituents or salts thereof.

  本发明提供了具有抗肿瘤作用的化合物，即具有不同取代基的以下式(I)或(Ia)所表示的化合物，其中G和G1是缩合的三环杂环或其盐，以及具有不同取代基或其盐的以下式(Ib)所表示的化合物。