2-(4-Chloroanilino)-4-hydroxy-6-phenylpyrimidine-5-carbonitrile | 273920-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(4-Chloroanilino)-4-hydroxy-6-phenylpyrimidine-5-carbonitrile
• 英文别名: 2-(4-chloroanilino)-6-oxo-4-phenyl-1H-pyrimidine-5-carbonitrile
• CAS: 273920-44-8
• 化学式: C₁₇H₁₁ClN₄O
• 分子量: 322.754
• InChiKey: VQOGTUSUCNOWHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Chloroanilino)-4-hydroxy-6-phenylpyrimidine-5-carbonitrile 、 1-碘代丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以61%的产率得到2-(4-Chloroanilino)-4-phenyl-6-propoxypyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of a 2,4,6-trisubstituted 5-cyano-pyrimidine library and evaluation of its immunosuppressive activity in a Mixed Lymphocyte Reaction assay

  摘要：

  A series of novel pyrimidine analogues were synthesized and evaluated for immunosuppressive activity in the Mixed Lymphocyte Reaction assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. Systematic variation of the substituents at positions 2, 4 and 6 of the pyrimidine scaffold led to the discovery of 2-benzylthio-5-cyano-6-(4-methoxyphenyl)-4-morpholinopyrimidine with an IC50 value of 1.6 mu M in the MLR assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.032
• 作为产物：
  描述：

  氰乙酸乙酯 、 苯甲醛 、 N-(4-氯苯基)胍 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-(4-Chloroanilino)-4-hydroxy-6-phenylpyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of a 2,4,6-trisubstituted 5-cyano-pyrimidine library and evaluation of its immunosuppressive activity in a Mixed Lymphocyte Reaction assay

  摘要：

  A series of novel pyrimidine analogues were synthesized and evaluated for immunosuppressive activity in the Mixed Lymphocyte Reaction assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. Systematic variation of the substituents at positions 2, 4 and 6 of the pyrimidine scaffold led to the discovery of 2-benzylthio-5-cyano-6-(4-methoxyphenyl)-4-morpholinopyrimidine with an IC50 value of 1.6 mu M in the MLR assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.032