4-adamantan-1-yl-2-chloro-6-(4-methylpiperazin-1-yl)pyrimidine | 1070217-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-adamantan-1-yl-2-chloro-6-(4-methylpiperazin-1-yl)pyrimidine
• CAS: 1070217-48-9
• 化学式: C₁₉H₂₇ClN₄
• 分子量: 346.903
• InChiKey: KPQKAKNJYPBGBM-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  4-adamantan-1-yl-2-chloro-6-(4-methylpiperazin-1-yl)pyrimidine 在 氨 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以20%的产率得到4-adamantan-1-yl-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylamine
  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：

  N-甲基哌嗪 、 4-adamantan-1-yl-2,6-dichloropyrimidine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以73%的产率得到4-adamantan-1-yl-2-chloro-6-(4-methylpiperazin-1-yl)pyrimidine
  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