4-(5-phenyl[1,3.4]oxadiazol-2-yl)-10H-acridin-9-one | 1147097-35-5

• 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-(5-phenyl[1,3.4]oxadiazol-2-yl)-10H-acridin-9-one
• 英文别名: 4-(5-phenyl-1,3,4-oxadiazol-2-yl)-10H-acridin-9-one
• CAS: 1147097-35-5
• 化学式: C₂₁H₁₃N₃O₂
• 分子量: 339.353
• InChiKey: NMQPOCXVIWZKPU-UHFFFAOYSA-N

物化性质

• 沸点：
  575.2±60.0 °C(predicted)
• 密度：
  1.313±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N'-benzylidene-9-oxo-9,10-dihydroacridine-4-carbohydrazide 在 溴 、 sodium acetate 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 以65%的产率得到4-(5-phenyl[1,3.4]oxadiazol-2-yl)-10H-acridin-9-one
  参考文献：
  名称：

  Synthesis and Properties of Novel Biologically Interesting Polycyclic 1,3,4-Oxadiazoles Containing Acridine/Acridone Moieties

  摘要：

  A series of polycyclic 1,3,4-oxadiazoles bearing acridine and acridone pharmacophores were synthesized as potential noncovalent DNA-binding and antitumor agents. The synthesis of oxadiazoles with acridone moiety was performed exploring oxidative cyclization of corresponding aldimines via bromine and the acridine derivatives by cyclization of acylthiosemicarbazides with mercuric oxide. The spectroscopic properties of the compounds in the case of acridonoxadiazoles showed an efficient binding activity to DNA (K = 5.3-9.2 x 10(4) M-1), whereas the acridine analogues are suitable as biomarkers. The structure of compounds were characterized by spectral methods (UV-vis, IR, H-1, C-13, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO).

  DOI：

  10.3987/com-08-s(f)80

文献信息

• Synthesis and Properties of Novel Biologically Interesting Polycyclic 1,3,4-Oxadiazoles Containing Acridine/Acridone Moieties
  作者：Ján Imrich、Zdenka Fröhlichová、Jana Tomaščiková、Pavol Kristian、Ivan Danihel、Stanislav Böhm、Danica Sabolová、Mária Kožurková、Karel D. Klika

  DOI：10.3987/com-08-s(f)80

  日期：——

  A series of polycyclic 1,3,4-oxadiazoles bearing acridine and acridone pharmacophores were synthesized as potential noncovalent DNA-binding and antitumor agents. The synthesis of oxadiazoles with acridone moiety was performed exploring oxidative cyclization of corresponding aldimines via bromine and the acridine derivatives by cyclization of acylthiosemicarbazides with mercuric oxide. The spectroscopic properties of the compounds in the case of acridonoxadiazoles showed an efficient binding activity to DNA (K = 5.3-9.2 x 10(4) M-1), whereas the acridine analogues are suitable as biomarkers. The structure of compounds were characterized by spectral methods (UV-vis, IR, H-1, C-13, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO).