4-N-cyclohexyl-6-methyl-2-N-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine | 1348084-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-N-cyclohexyl-6-methyl-2-N-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• CAS: 1348084-98-9
• 化学式: C₂₁H₃₀N₄O₃
• 分子量: 386.494
• InChiKey: PWGABFFTYSZIDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄胺 、 2-chloro-4-cyclohexylamino-6-methylpyrimidine 以 异丙醇 为溶剂， 反应 1.0h， 以55%的产率得到4-N-cyclohexyl-6-methyl-2-N-[(3,4,5-trimethoxyphenyl)methyl]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