6-methyl-N4-phenyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine | 1207425-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-methyl-N4-phenyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine
• 英文别名: 6-methyl-4-N-phenyl-2-N-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine
• CAS: 1207425-13-5
• 化学式: C₁₇H₁₇N₅
• 分子量: 291.355
• InChiKey: FHFLPMVCAWECFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨甲基吡啶 、 2-chloro-6-methyl-N-phenylpyrimidin-4-amine 以 异丙醇 为溶剂， 反应 1.0h， 以72%的产率得到6-methyl-N4-phenyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of novel 2,4-diaminopyrimidines

  摘要：

  Two sets of diaminopyrimidines, totalling 45 compounds, were synthesized and assayed against Plasmodium falciparum. The SAR was relatively shallow, with only the presence of a 2-(pyrrolidin-1-yl)ethyl group at R-2 significantly affecting activity. A subsequent series addressed high Log D values by introducing more polar side groups, with the most active compounds possessing diazepine and N-benzyl-4-aminopiperidyl groups at R-1/R-2. A final series attempted to address high in vitro microsomal clearance by replacing the C6-Me group with CF3, however antiplasmodial activity decreased without any improvement in clearance. The C6-CF3 group decreased hERG inhibition, probably as a result of decreased amine basicity at C2/C4. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.133

文献信息

• Synthesis and antiplasmodial activity of novel 2,4-diaminopyrimidines
  作者：Derek C. Martyn、Amarjit Nijjar、Cassandra A. Celatka、Ralph Mazitschek、Joseph F. Cortese、Erin Tyndall、Hanlan Liu、Maria M. Fitzgerald、Thomas J. O’Shea、Sanjay Danthi、Jon Clardy

  DOI：10.1016/j.bmcl.2009.10.133

  日期：2010.1

  Two sets of diaminopyrimidines, totalling 45 compounds, were synthesized and assayed against Plasmodium falciparum. The SAR was relatively shallow, with only the presence of a 2-(pyrrolidin-1-yl)ethyl group at R-2 significantly affecting activity. A subsequent series addressed high Log D values by introducing more polar side groups, with the most active compounds possessing diazepine and N-benzyl-4-aminopiperidyl groups at R-1/R-2. A final series attempted to address high in vitro microsomal clearance by replacing the C6-Me group with CF3, however antiplasmodial activity decreased without any improvement in clearance. The C6-CF3 group decreased hERG inhibition, probably as a result of decreased amine basicity at C2/C4. (C) 2009 Elsevier Ltd. All rights reserved.