4-anilino[1]benzothieno[2,3-d]pyrimidine | 1228939-85-2

• 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: 4-anilino[1]benzothieno[2,3-d]pyrimidine
• 英文别名: 4-Anilinobenzo[b]thieno[2,3-d]pyrimidine；N-phenyl-[1]benzothiolo[2,3-d]pyrimidin-4-amine
• CAS: 1228939-85-2
• 化学式: C₁₆H₁₁N₃S
• 分子量: 277.349
• InChiKey: IWDVGHBCUBNOJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯胺 、 4-chlorobenzo[4,5]thieno[2,3-d]pyrimidine 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-anilino[1]benzothieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and study of antiproliferative activity of novel thienopyrimidines on glioblastoma cells

  摘要：

  The receptor tyrosine kinases (for example EGFR, PDGFR, VEGFR) are a transmembrane protein family which plays a crucial role in tumor growth, survival, metastasis dissemination and angiogenesis. During the past 10 years, many tyrosine kinase inhibitors (TKIs) have been approved for cancer treatment (imatinib, gefitinib, erlotinib, sunitinib, sorafenib). These compounds generally possess a pyrrolo- or pyrimido- pyrimidine scaffold or approaching molecular structure. We synthesized 10 thienopyrimidine compounds (including 5 newly synthesized) whose scaffold is very similar to the agents cited above. The cytotoxicity of these agents was evaluated using a MTT assay and a flow cytometry technique on glioblastoma cell lines. Two compounds showed a similar cytotoxicity to the standard anti-EGFR gefitinib (IC50: gefitinib = 51.9 mu M, 6b = 61.8 mu M, 6c = 41.2 mu M), suggesting a blockade of the EGFR pathway by binding to the TK receptor.

  DOI：

  10.1016/j.ejmech.2010.02.032

文献信息

• Synthesis and study of antiproliferative activity of novel thienopyrimidines on glioblastoma cells
  作者：Stéphane Pédeboscq、Denis Gravier、Françoise Casadebaig、Geneviève Hou、Arnaud Gissot、Francesca De Giorgi、François Ichas、Jean Cambar、Jean-Paul Pometan

  DOI：10.1016/j.ejmech.2010.02.032

  日期：2010.6

  The receptor tyrosine kinases (for example EGFR, PDGFR, VEGFR) are a transmembrane protein family which plays a crucial role in tumor growth, survival, metastasis dissemination and angiogenesis. During the past 10 years, many tyrosine kinase inhibitors (TKIs) have been approved for cancer treatment (imatinib, gefitinib, erlotinib, sunitinib, sorafenib). These compounds generally possess a pyrrolo- or pyrimido- pyrimidine scaffold or approaching molecular structure. We synthesized 10 thienopyrimidine compounds (including 5 newly synthesized) whose scaffold is very similar to the agents cited above. The cytotoxicity of these agents was evaluated using a MTT assay and a flow cytometry technique on glioblastoma cell lines. Two compounds showed a similar cytotoxicity to the standard anti-EGFR gefitinib (IC50: gefitinib = 51.9 mu M, 6b = 61.8 mu M, 6c = 41.2 mu M), suggesting a blockade of the EGFR pathway by binding to the TK receptor.