5-(benzylaminomethylene)-N,N'-dimethylbarbituric acid

• 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-(benzylaminomethylene)-N,N'-dimethylbarbituric acid
• 英文别名: 5-(benzylaminomethylene)-1,3-dimethylpyrimidine-2,4,6-trione；5-((benzylamino)methylene)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione；5-[(benzylamino)methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• 化学式: C₁₄H₁₅N₃O₃
• mdl: MFCD00127313
• 分子量: 273.291
• InChiKey: YJKMMFLHVRELSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 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：
  0.214
• 拓扑面积：
  69.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 以 正丁醇 为溶剂， 反应 1.5h， 生成 5-(benzylaminomethylene)-N,N'-dimethylbarbituric acid
  参考文献：
  名称：

  Reaction of 2-Chloro-1-alkyl-1H-Indol-3-carbaldehydes with Barbituric Acids and 5-Methyl-2-phenyl-2,4-dihydropyrazol-3-one. Formation of Compound with Extremely Short Intramolecular Hydrogen Bond in Eight-Membered Pseudocycle

  摘要：

  New indolin-2-one derivatives, containing in its molecules eight-membered pseudo-cycle with unusually short intramolecular hydrogen bond in OHO-bridge have been synthesized by reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehyde with barbituric acids or 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Under the action of amines they undergo fragmentation to 5-aminomethylenebarbituric acids or 4-aminomethylenepyrazolones and 1-alkyl-1,3-dihydroindo1-2-ones.

  DOI：

  10.3987/com-14-13135

文献信息

• N,N-Dimethylformamide-Promoted Reaction of Isocyanides and Barbituric acids: An Easy Synthesis of 5-[(Alkyl or Arylamino)Methylene]Barbituric Acids
  作者：Mohammad Bagher Teimouri、Ahmad Tayyebi

  DOI：10.3184/030823410x12682371167951

  日期：2010.3

  the reaction of alkyl or arylisocyanides with barbituric acid derivatives which led to 5-[(alkyl or arylamino)methylene]barbituric acids in good yields at room temperature. The workup of reactions was very simple and the crude products were sufficiently pure to be used without further purification. This procedure provides an alternative method for the synthesis of aminomethylenebarbituric acids.

  N,N-二甲基甲酰胺促进烷基或芳基异氰化物与巴比妥酸衍生物的反应，从而在室温下以良好的产率生成5-[(烷基或芳基氨基)亚甲基]巴比妥酸。反应的后处理非常简单，粗产物足够纯，无需进一步纯化即可使用。该程序提供了一种合成氨基亚甲基巴比妥酸的替代方法。
• Synthesis and Urease Inhibitory Activity of Some 5-Aminomethylene Barbituric/Thiobarbituric Acid Derivatives
  作者：Mehdi Asadi、Mohammad Mahdavi、Shabnam Mahernia、Zahra Rezaei、Maliheh Safavi、Mina Saeedi、Massoud Amanlou

  DOI：10.2174/1570180814666170727142928

  日期：2018.3.12

  wide spectrum of 5-aminomethylene barbituric/ thiobarbituric acid derivatives was synthesized and evaluated for their Jack bean urease inhibitory activity. Methods: Among the synthesized compounds, 5-cyclohexylaminomethylene barbituric acid (3a) showed the most potent activity (IC50 = 25.8 µM), 4 times more potent than hydroxyurea (IC50 = 100.0 µM) and a similar activity to thiourea (IC50 = 22.0 µM), both

  背景：在这项工作中，合成了多种5-氨基亚甲基巴比妥酸/硫代巴比妥酸衍生物，并评估了它们对杰克豆脲酶的抑制活性。 方法：在合成的化合物中，5-环己基氨基亚甲基巴比妥酸（3a）的活性最高（IC50 = 25.8 µM），效力是羟基脲（IC50 = 100.0 µM）的4倍，活性与硫脲（IC50 = 22.0 µM）类似），均作为参考药物。 结果和结论：此外，对接研究的结果与体外测定的结果吻合良好。
• Yavari; Hazeri; Maghsoodlou, Journal of Chemical Research - Part S, 2001, # 7, p. 272 - 273
  作者：Yavari、Hazeri、Maghsoodlou、Moradi

  DOI：——

  日期：——
• Reaction of 2-Chloro-1-alkyl-1H-Indol-3-carbaldehydes with Barbituric Acids and 5-Methyl-2-phenyl-2,4-dihydropyrazol-3-one. Formation of Compound with Extremely Short Intramolecular Hydrogen Bond in Eight-Membered Pseudocycle
  作者：Konstantin F. Suzdalev、Maria N. Babakova、Victor G. Kartsev、Konstantin A. Krasnov

  DOI：10.3987/com-14-13135

  日期：——

  New indolin-2-one derivatives, containing in its molecules eight-membered pseudo-cycle with unusually short intramolecular hydrogen bond in OHO-bridge have been synthesized by reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehyde with barbituric acids or 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Under the action of amines they undergo fragmentation to 5-aminomethylenebarbituric acids or 4-aminomethylenepyrazolones and 1-alkyl-1,3-dihydroindo1-2-ones.