2-苯甲酰甲基-1,2,4-三嗪-3,5-二酮 | 61959-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-苯甲酰甲基-1,2,4-三嗪-3,5-二酮
• 英文名称: 2-(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: 2-(2-oxo-2-phenyl-ethyl)-2H-[1,2,4]triazine-3,5-dione；2-(2-Oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione；2-phenacyl-1,2,4-triazine-3,5-dione
• CAS: 61959-06-6
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: KBSINQJWPBSPOI-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苯甲酰甲基-1,2,4-三嗪-3,5-二酮 、 2-溴甲基丙烯酸乙酯 在 对苯二酚 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以72.5%的产率得到2-[(4-methylene-5-oxo-2-phenyltetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores

  摘要：

  A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris.

  DOI：

  10.1007/s00044-010-9438-7
• 作为产物：
  描述：

  6-氮杂脲嘧啶 、 2-溴苯乙酮 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-苯甲酰甲基-1,2,4-三嗪-3,5-二酮
  参考文献：
  名称：

  一些新型腙无环核苷类似物的合成。

  摘要：

  描述了类似于咪康唑支架的新型腙无环核苷的合成。在这一系列无环核苷中，嘧啶以及嘌呤和其他唑类衍生物取代了咪康唑中的咪唑功能，并且使用苯肼将醚基团替换为腙部分。为了解释 (E)-腙衍生物而不是 (Z)-异构体的主要形成，进行了 PM3 半经验量子力学计算，表明 (E)-异构体具有较低的形成热。

  DOI：

  10.3762/bjoc.6.49

文献信息

• Structure–cytotoxicity relationship of a novel series of miconazole-like compounds
  作者：Reza Yousefi、Ali Khalafi-Nezhad、Mohammad Navid Soltani Rad、Somayeh Behrouz、Farhad Panahi、Mansoore Esmaili、Sayed Mahmoud Ghaffari、Ali Niazi、Ali Akbar Moosavi-Movahedi

  DOI：10.1007/s00044-011-9716-z

  日期：2012.8

  In the current study, two novel classes of the carboacyclic nucleosides having miconazole-like scaffolds as imidazole- and pyrimidine-based compounds were examined for their cytotoxic properties. The aim was to establish a relation between cytotoxic activity and nature of the synthetic compounds. While Escherichia coli (DH5 alpha) and human erythromyeloblastoid leukemia cell line (K562) were the target cells, depending on the type of substitution made, ranges of antibacterial and antineoplastic activities were observed. Also the electron-donating and electron-accepting properties of the ligands were proved to play a crucial role in their cytotoxic activities. Accordingly, the substitutions associated with the marked improvement of cytotoxic activities can be considered as the significant point in construction of new generation of either antibacterial or antineoplastic agents.