4-(benzo[d]oxazol-2-yl)-2-chloroaniline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(benzo[d]oxazol-2-yl)-2-chloroaniline
• 英文别名: 4-(1,3-Benzoxazol-2-yl)-2-chloroaniline
• 化学式: C₁₃H₉ClN₂O
• mdl: MFCD00781817
• 分子量: 244.68
• InChiKey: AHXIIHHSMKTBRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzo[d]oxazol-2-yl)-2-chloroaniline 、 偏苯三酸酐 在 溶剂黄146 作用下， 以73%的产率得到2-[4-(benzo[d]oxazol-2-yl)-2-chlorophenyl]-1,3-dioxoisoindoline-5-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of new benzoxazole/benzothiazole-phthalimide hybrids as antitumor-apoptotic agents

  摘要：

  Herein, we synthesized a series of twelve benzoxazole and benzothiazole derivatives incorporated with phthalimide core as anticancer agents. The most active compounds were 5a and 5g against HepG2 and MCF7 cell lines with IC50 = 0.011 and 0.006 mu M, respectively.They evaluated against EGFR and HER2 enzymes. From cell cycle analysis, it was observed that test compounds exerted pre G1 apoptosis and cell cycle arrest at G2/M phase. The achieved results suggested that apoptosis was due to activation of caspase-7 and caspase-9. EGFR was chosen as a biological target for carrying molecular modeling study for the newly synthesized compounds.

  DOI：

  10.1016/j.bioorg.2019.102978
• 作为产物：
  描述：

  3-氯-4-氨基苯甲酸 、 2-氨基苯酚 在 polyphosphoric acid 作用下， 反应 4.0h， 以72%的产率得到4-(benzo[d]oxazol-2-yl)-2-chloroaniline
  参考文献：
  名称：

  Design and synthesis of new benzoxazole/benzothiazole-phthalimide hybrids as antitumor-apoptotic agents

  摘要：

  Herein, we synthesized a series of twelve benzoxazole and benzothiazole derivatives incorporated with phthalimide core as anticancer agents. The most active compounds were 5a and 5g against HepG2 and MCF7 cell lines with IC50 = 0.011 and 0.006 mu M, respectively.They evaluated against EGFR and HER2 enzymes. From cell cycle analysis, it was observed that test compounds exerted pre G1 apoptosis and cell cycle arrest at G2/M phase. The achieved results suggested that apoptosis was due to activation of caspase-7 and caspase-9. EGFR was chosen as a biological target for carrying molecular modeling study for the newly synthesized compounds.

  DOI：

  10.1016/j.bioorg.2019.102978