5,6-bis(4-chlorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one | 1437869-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 5,6-bis(4-chlorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one
• CAS: 1437869-96-9
• 化学式: C₁₈H₁₀Cl₂N₂OS
• 分子量: 373.262
• InChiKey: DMDBKYDBUSSSDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  515.9±60.0 °C(predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.75
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,6-bis(4-chlorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one 在 三氯氧磷 作用下， 以 正丁醇 为溶剂， 反应 6.0h， 生成 5,6-bis(4-chlorophenyl)-N-cyclopropylthieno[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 3,4,5-trisubstituted aminothiophenes as inhibitors of p53–MDM2 interaction. Part 2

  摘要：

  Five series of novel 3,4,5-trisubstituted aminothiophene derivatives and analogs were designed and synthesized based on our previous studies. All target compounds were evaluated for their p53-MDM2 binding inhibitory activities and anti-proliferation activities against A549 and PC3 tumor cell lines. Twelve compounds displayed comparable p53-MDM2 binding inhibitory activities to that of Nutlin-3. Among them, compound 7a exhibited marked binding affinity (IC50 = 0.086 mu M). In addition, most target compounds showed potent anti-proliferation activities with IC50 values at low micromolar level. A good selective profile for wild-type p53 expression cell line was also observed. Molecular docking analysis was performed as well to predict possible binding modes of target compounds with MDM2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.070
• 作为产物：
  描述：

  2-(1,2-bis(4-chlorophenyl)ethylidene)malononitrile 在 乙酸酐 、 sulfur 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 5,6-bis(4-chlorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 3,4,5-trisubstituted aminothiophenes as inhibitors of p53–MDM2 interaction. Part 2

  摘要：

  Five series of novel 3,4,5-trisubstituted aminothiophene derivatives and analogs were designed and synthesized based on our previous studies. All target compounds were evaluated for their p53-MDM2 binding inhibitory activities and anti-proliferation activities against A549 and PC3 tumor cell lines. Twelve compounds displayed comparable p53-MDM2 binding inhibitory activities to that of Nutlin-3. Among them, compound 7a exhibited marked binding affinity (IC50 = 0.086 mu M). In addition, most target compounds showed potent anti-proliferation activities with IC50 values at low micromolar level. A good selective profile for wild-type p53 expression cell line was also observed. Molecular docking analysis was performed as well to predict possible binding modes of target compounds with MDM2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.070