6-(6,8-dichloro-2H-1,3-benzoxazin-3(4H)-yl)-2-phenyl-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-(6,8-dichloro-2H-1,3-benzoxazin-3(4H)-yl)-2-phenyl-4H-chromen-4-one
• 英文别名: 6-(6,8-Dichloro-2,4-dihydro-1,3-benzoxazin-3-yl)-2-phenylchromen-4-one；6-(6,8-dichloro-2,4-dihydro-1,3-benzoxazin-3-yl)-2-phenylchromen-4-one
• 化学式: C₂₃H₁₅Cl₂NO₃
• 分子量: 424.283
• InChiKey: ASYNGEXLXBMBKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-氨基黄酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 6-(6,8-dichloro-2H-1,3-benzoxazin-3(4H)-yl)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of 1,3-benzoxazine derivatives as potential anticancer agents

  摘要：

  A series of 6 and/or 8-substituted derivatives of 1,3-benzoxazines, having flavone moiety at 3-position, have been synthesized. For synthesis of the compounds, 6 or/and 8-substituted saliscylaldehydes were reacted with aminoflavone followed by reduction, and CHCl3/HCHO promoted cyclization to give corresponding aminoflavone precursors which provided the desired 1,3-benzoxazine skeleton. Cytotoxic effects of the synthesized compounds were investigated in vitro against human breast cancer (MCF-7) cell lines. Among the compounds tested, methyl (3f and 6f), methoxy (3h, 3i, and 6h), and chloro (3d) derivatives were found to be most potent with IC50 values of 14.3, 14.9, 17.1, 8.03, 12.1, and 12.03 mu M, respectively. Molecular docking studies of most active compounds of the series revealed that they bind to a narrow hydrophobic pocket of the N-terminal chain in the ATP binding site of EGFR.

  DOI：

  10.1007/s00044-013-0534-3

文献信息

• Synthesis, biological evaluation and molecular docking studies of 1,3-benzoxazine derivatives as potential anticancer agents
  作者：Vikas Garg、Ankit Kumar、Anurag Chaudhary、Saurabh Agrawal、Praveen Tomar、K. K. Sreenivasan

  DOI：10.1007/s00044-013-0534-3

  日期：2013.11

  A series of 6 and/or 8-substituted derivatives of 1,3-benzoxazines, having flavone moiety at 3-position, have been synthesized. For synthesis of the compounds, 6 or/and 8-substituted saliscylaldehydes were reacted with aminoflavone followed by reduction, and CHCl3/HCHO promoted cyclization to give corresponding aminoflavone precursors which provided the desired 1,3-benzoxazine skeleton. Cytotoxic effects of the synthesized compounds were investigated in vitro against human breast cancer (MCF-7) cell lines. Among the compounds tested, methyl (3f and 6f), methoxy (3h, 3i, and 6h), and chloro (3d) derivatives were found to be most potent with IC50 values of 14.3, 14.9, 17.1, 8.03, 12.1, and 12.03 mu M, respectively. Molecular docking studies of most active compounds of the series revealed that they bind to a narrow hydrophobic pocket of the N-terminal chain in the ATP binding site of EGFR.