2-(((1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(2-fluorophenyl)-6-phenylpyrimidin-4-amine | 1622873-78-2

• 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-(((1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(2-fluorophenyl)-6-phenylpyrimidin-4-amine
• 英文别名: 2-(1H-benzimidazol-2-ylmethylsulfanyl)-N-(2-fluorophenyl)-6-phenylpyrimidin-4-amine
• CAS: 1622873-78-2
• 化学式: C₂₄H₁₈FN₅S
• 分子量: 427.505
• InChiKey: ZAYXZOPWAPMRNN-UHFFFAOYSA-N

物化性质

• 沸点：
  685.521±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.414±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯甲基苯并咪唑 在 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 12.5h， 生成 2-(((1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(2-fluorophenyl)-6-phenylpyrimidin-4-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrimidine–benzimidazol hybrids as potential anticancer agents

  摘要：

  A series of pyrimidine-benzimidazol hybrids was synthesized and evaluated for anticancer activity on four human cancer cell lines including MCF-7, MGC-803, EC-9706 and SMMC-7721. Some of the synthesized compounds exhibited moderate to potent activity against MGC-803 and MCF-7. Among them, compounds 5a-b and 6a-b showed most effective activity. Compounds 5b and 6b were more cytotoxic than 5-fluorouracil against all tested four human cancer cell lines, with IC50 values ranging from 2.03 to 10.55 μM and 1.06 to 12.89 μM, respectively. Flow cytometry analysis demonstrated that treatment of MGC-803 with 6b led to cell cycle arrest at G2/M phase accompanied by an increase in apoptotic cell death.

  DOI：

  10.1016/j.bmcl.2014.06.050

文献信息

• Synthesis and biological evaluation of novel pyrimidine–benzimidazol hybrids as potential anticancer agents
  作者：Kun-Peng Shao、Xu-Yao Zhang、Peng-Ju Chen、Deng-Qi Xue、Peng He、Li-Ying Ma、Jia-Xin Zheng、Qiu-Rong Zhang、Hong-Min Liu

  DOI：10.1016/j.bmcl.2014.06.050

  日期：2014.8

  A series of pyrimidine-benzimidazol hybrids was synthesized and evaluated for anticancer activity on four human cancer cell lines including MCF-7, MGC-803, EC-9706 and SMMC-7721. Some of the synthesized compounds exhibited moderate to potent activity against MGC-803 and MCF-7. Among them, compounds 5a-b and 6a-b showed most effective activity. Compounds 5b and 6b were more cytotoxic than 5-fluorouracil against all tested four human cancer cell lines, with IC50 values ranging from 2.03 to 10.55 μM and 1.06 to 12.89 μM, respectively. Flow cytometry analysis demonstrated that treatment of MGC-803 with 6b led to cell cycle arrest at G2/M phase accompanied by an increase in apoptotic cell death.