1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidine-5-carbaldehyde phenylhydrazone | 100796-68-7

• 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: 1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidine-5-carbaldehyde phenylhydrazone
• 英文别名: 1,3-Dimethyl-5-phenylhydrazinomethylen-barbitursaeure；1,3-dimethyl-5-[(2-phenylhydrazinyl)methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 100796-68-7
• 化学式: C₁₃H₁₄N₄O₃
• 分子量: 274.279
• InChiKey: LGZXDAOKXJNCFK-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 沸点：
  319.4±52.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.75
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 、 苯肼 以 甲醇 为溶剂， 以80%的产率得到1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidine-5-carbaldehyde phenylhydrazone
  参考文献：
  名称：

  Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ – Potential candidates for multi drug resistance modulation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.12.033

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.