3-fluoro-4-[5-(5-methylthiophen-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxyaniline | 1321618-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-fluoro-4-[5-(5-methylthiophen-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxyaniline
• CAS: 1321618-72-7
• 化学式: C₁₇H₁₂FN₃OS₂
• 分子量: 357.432
• InChiKey: AHWXQOSOFCJARL-UHFFFAOYSA-N

物化性质

• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1.443±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.03
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-2-氧代-1,2-二氢吡啶-3-羧酸 、 3-fluoro-4-[5-(5-methylthiophen-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxyaniline 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到N-(3-fluoro-4-(5-(5-methylthiophen-2-yl)thieno[2,3-d]pyrimidin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  Discovery of novel c-Met kinase inhibitors bearing a thieno[2,3-d]pyrimidine or furo[2,3-d]pyrimidine scaffold

  摘要：

  A series of thieno[2,3-d]pyrimidines and furo[2,3-d] pyrimidines were synthesized and evaluated for the c-Met inhibition. Thieno[2,3-d]pyrimidine 6b stood out as the most potent showing an IC(50) of 35.7 nM. This compound displayed high inhibitory effect on cell proliferation in BaF3-TPR-Met cells and showed high selectivity for c-Met family against other 14 tested kinases. However, compound 6b was found ineffective in the c-Met-dependent U-87MG human gliobastoma xenograft model that may be relevant to its poor PK profile. (C) 2011 Elsevier Ltd. All rights

  DOI：

  10.1016/j.bmc.2011.05.038
• 作为产物：
  描述：

  4-Chloro-5-(5-methylthiophen-2-yl)thieno[2,3-d]pyrimidine 、 4-氨基-2-氟苯酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-fluoro-4-[5-(5-methylthiophen-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxyaniline
  参考文献：
  名称：

  Discovery of novel c-Met kinase inhibitors bearing a thieno[2,3-d]pyrimidine or furo[2,3-d]pyrimidine scaffold

  摘要：

  A series of thieno[2,3-d]pyrimidines and furo[2,3-d] pyrimidines were synthesized and evaluated for the c-Met inhibition. Thieno[2,3-d]pyrimidine 6b stood out as the most potent showing an IC(50) of 35.7 nM. This compound displayed high inhibitory effect on cell proliferation in BaF3-TPR-Met cells and showed high selectivity for c-Met family against other 14 tested kinases. However, compound 6b was found ineffective in the c-Met-dependent U-87MG human gliobastoma xenograft model that may be relevant to its poor PK profile. (C) 2011 Elsevier Ltd. All rights

  DOI：

  10.1016/j.bmc.2011.05.038