4-(2-(9-oxoacridin-10(9H)-yl)acetamido)benzoic acid | 1572652-25-5

• 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: 4-(2-(9-oxoacridin-10(9H)-yl)acetamido)benzoic acid
• 英文别名: 4-[[2-(9-Oxoacridin-10-yl)acetyl]amino]benzoic acid；4-[[2-(9-oxoacridin-10-yl)acetyl]amino]benzoic acid
• CAS: 1572652-25-5
• 化学式: C₂₂H₁₆N₂O₄
• 分子量: 372.38
• InChiKey: SEIPLRHMBRHXIE-UHFFFAOYSA-N

物化性质

• 熔点：
  265-267 °C
• 沸点：
  680.2±55.0 °C(predicted)
• 密度：
  1.406±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对氨基苯甲酸 在 sodium acetate 、 sodium hydride 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.5h， 生成 4-(2-(9-oxoacridin-10(9H)-yl)acetamido)benzoic acid
  参考文献：
  名称：

  Synthesis, cytotoxic study and docking based multidrug resistance modulator potential analysis of 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamides

  摘要：

  The present study describes the synthesis of fifteen 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamide derivatives (13a-o) through condensation of 2-chloro-N-phenyl acetamides (12a-o) with acridone molecule (10). All the synthesized compounds were screened for their anti-cancer activity against three diverse cell lines including breast (MCF-7), cervical (HeLa) and lung adenocarcinoma (A-549) employing standard MTT assay. Among synthesized molecules, 13k and 13l showed good cytotoxicity activity against considered three cancer cell lines. Additionally, in silico studies of multidrug resistance modulator (MDR) effects of these compounds was performed by docking simulation in the ATP binding site of P-gp. The results of docking simulation displayed important interactions of these molecules in the active site of this protein and predicted their MDR modulator behavior.

  DOI：

  10.1016/j.ejmech.2014.04.030

文献信息

• Synthesis, cytotoxic study and docking based multidrug resistance modulator potential analysis of 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamides
  作者：Rajesh Kumar、Maninder Kaur、Malkeet Singh Bahia、Om Silakari

  DOI：10.1016/j.ejmech.2014.04.030

  日期：2014.6

  The present study describes the synthesis of fifteen 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamide derivatives (13a-o) through condensation of 2-chloro-N-phenyl acetamides (12a-o) with acridone molecule (10). All the synthesized compounds were screened for their anti-cancer activity against three diverse cell lines including breast (MCF-7), cervical (HeLa) and lung adenocarcinoma (A-549) employing standard MTT assay. Among synthesized molecules, 13k and 13l showed good cytotoxicity activity against considered three cancer cell lines. Additionally, in silico studies of multidrug resistance modulator (MDR) effects of these compounds was performed by docking simulation in the ATP binding site of P-gp. The results of docking simulation displayed important interactions of these molecules in the active site of this protein and predicted their MDR modulator behavior.