5-(N'-(2,4-dinitrophenyl)-hydrazinomethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione | 105474-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(N'-(2,4-dinitrophenyl)-hydrazinomethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidine-5-carbaldehyde (2,4-dinitro-phenyl)-hydrazone；1,3-Dimethyl-5-<(2,4-dinitro-phenyl)-hydrazinomethylen>-barbitursaeure；1,3-Dimethyl-5-dinitrophenylhydrazinomethylen-barbitursaeure；5-[[2-(2,4-dinitrophenyl)hydrazinyl]methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 105474-89-3
• 化学式: C₁₃H₁₂N₆O₇
• 分子量: 364.274
• InChiKey: HFDKWKMWJKJPFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  168.03
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 5-(N'-(2,4-dinitrophenyl)-hydrazinomethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  制备5-甲酰基-和5-乙酰基巴比妥酸，包括相应的席夫碱和苯基hydr

  摘要：

  描述了用于巴比妥酸衍生物的甲酰化和乙酰化的简单，有效和高产率的合成方法。在与ω-氨基链烷酸和硝基苯肼的高收率缩合反应中，生成的5-酰基巴比妥酸被转化为相应的席夫碱。

  DOI：

  10.1016/s0040-4039(01)01830-5

文献信息

• Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ – Potential candidates for multi drug resistance modulation
  作者：Palwinder Singh、Jatinder Kaur、Atul Bhardwaj

  DOI：10.1016/j.ejmech.2009.12.033

  日期：2010.3

  A number of barbituric acids with appropriate substituent at C-5 position were synthesized and investigated for their interactions with p-gp and Mg2+. Compounds 5, 6, 8-10, 12-14 and 16 increased the basal activity of p-gp by more than 50% at 0.05 mu M concentration. Molecular docking indicate a number of H-bond interactions between these molecules and the amino acid residues of ATP binding site of p-gp. These molecules also showed appreciable interactions with Mg2+, an important component of efflux pump. All the results of these investigations favor the suitability of barbituric acids toward MDR modulation. (C) 2009 Elsevier Masson SAS. All rights reserved.