3-(1,3-benzoxazol-2-yl)-2-chloroquinoline | 132279-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(1,3-benzoxazol-2-yl)-2-chloroquinoline
• 英文别名: 2-chloro-3-(benzoxazolyl)quinoline；2-(2-Chloroquinolin-3-yl)benzo[d]oxazole；2-(2-chloroquinolin-3-yl)-1,3-benzoxazole
• CAS: 132279-91-5
• 化学式: C₁₆H₉ClN₂O
• 分子量: 280.713
• InChiKey: KZTQBMDVJKXEOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 、 2-氨基苯酚 在 silica chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以75%的产率得到3-(1,3-benzoxazol-2-yl)-2-chloroquinoline
  参考文献：
  名称：

  In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors

  摘要：

  A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 +/- 0.16 mu M, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.

  DOI：

  10.1016/j.bioorg.2019.103382