4-((6-((4-aminophenyl)amino)-5-nitropyrimidin-4-yl)amino)benzimidamide

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-((6-((4-aminophenyl)amino)-5-nitropyrimidin-4-yl)amino)benzimidamide
• 英文别名: 4-[[6-(4-Aminoanilino)-5-nitropyrimidin-4-yl]amino]benzenecarboximidamide；4-[[6-(4-aminoanilino)-5-nitropyrimidin-4-yl]amino]benzenecarboximidamide
• 化学式: C₁₇H₁₆N₈O₂
• 分子量: 364.366
• InChiKey: GUFPUVFFFWHLRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-aminobenzamidine dihydrochloride 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 4-((6-((4-aminophenyl)amino)-5-nitropyrimidin-4-yl)amino)benzimidamide
  参考文献：
  名称：

  Discovery and structure–activity analysis of 4-((5-nitropyrimidin-4-yl)amino)benzimidamide derivatives as novel protein arginine methyltransferase 1 (PRMT1) inhibitors

  摘要：

  Despite a potential application of PRMT1 inhibitors in cancer treatment, very few of PRMT1 inhibitors have been reported. To obtain novel potent PRMT1 inhibitors, structure optimizations towards a hit compound, 4-((6-chloro-5-nitropyrimidin-4-yl)amino)benzimidamide, were carried out. A series of 4-((5-nitropyrimidin-4-yl)amino)benzimidamide derivatives were synthesized. Structure-activity relationship analysis led to the discovery of a number of PRMT1 inhibitors. The most potent compound corresponds to compound 6d, which showed an IC50 value of 2.0 mu M against PRMT1. This compound also displayed a considerable anti-proliferative activity against three tumor cell lines, DLD-1, T24 and SH-SY-5Y, with IC50 values of 4.4 mu M, 13.1 mu M and 11.4 mu M, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.095