4-(4-methylpiperazin-1-yl)-6-pyrrolidin-1-ylpyrimidin-2-ylamine | 1028327-85-6

• 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-(4-methylpiperazin-1-yl)-6-pyrrolidin-1-ylpyrimidin-2-ylamine
• 英文别名: 4-(4-methylpiperazin-1-yl)-6-pyrrolidin-1-ylpyrimidin-2-amine
• CAS: 1028327-85-6
• 化学式: C₁₃H₂₂N₆
• 分子量: 262.358
• InChiKey: YSAYBGMJMWXFOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 4-氯-6-吡咯烷-1-基嘧啶-2-胺 在 N,N-二异丙基乙胺 作用下， 以 甲乙醚 为溶剂， 反应 16.0h， 以69%的产率得到4-(4-methylpiperazin-1-yl)-6-pyrrolidin-1-ylpyrimidin-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

文献信息

• Method for Pain Treatment
  申请人：Cowart Marlon D.

  公开号：US20080194538A1

  公开（公告）日：2008-08-14

  This invention discloses a method of treating pain by administering histamine H 4 receptor ligands and compositions comprising the same.

  这项发明揭示了一种通过给予组织胺H4受体配体和包含相同的组合物来治疗疼痛的方法。
• Triamino pyrimidines and pyridines as histamine H4 receptor modulators
  作者：Steven P. Meduna、Brad M. Savall、Hui Cai、James P. Edwards、Robin L. Thurmond、Patricia M. McGovern

  DOI：10.1016/j.bmcl.2011.03.017

  日期：2011.5

  Two series of triamino pyrimidines and a series of triamino pyridines have been synthesized and their structure-activity relationships evaluated for activity at the H-4 receptor in competitive binding and functional assays. Small structural changes in these three hetereoaromatic cores influenced the functional activity of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• US7985745B2
  申请人：——

  公开号：US7985745B2

  公开（公告）日：2011-07-26