2-[(4-bromophenyl)methylsulfanyl]-6-(4-methoxyphenyl)-4-oxo-1H-pyrimidine-5-carbonitrile | 1425973-96-1

• 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-bromophenyl)methylsulfanyl]-6-(4-methoxyphenyl)-4-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 1425973-96-1
• 化学式: C₁₉H₁₄BrN₃O₂S
• 分子量: 428.309
• InChiKey: RJZAHPLXKQNYJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.77
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  吗啉 、 2-[(4-bromophenyl)methylsulfanyl]-6-(4-methoxyphenyl)-4-oxo-1H-pyrimidine-5-carbonitrile 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以64%的产率得到2-[(4-Bromophenyl)methylsulfanyl]-4-(4-methoxyphenyl)-6-morpholin-4-ylpyrimidine-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：

  4-甲氧基苯甲醛 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 2-[(4-bromophenyl)methylsulfanyl]-6-(4-methoxyphenyl)-4-oxo-1H-pyrimidine-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