1,3-二甲基-2,4,6-三氧代-六氢-嘧啶-5-甲醛 | 42604-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1,3-二甲基-2,4,6-三氧代-六氢-嘧啶-5-甲醛
• 英文名称: 1,3-dimethyl-2,4,6-trioxohexahydropyrimidine-5-carbaldehyde
• 英文别名: 5-formyl-1,3-dimethyl-2,4,6-pyridinetrione；5-formyl-1,3-dimethylbarbituric acid；5-formyl-1,3-dimethylpyrimidine-2,4,6-trione；1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidine-5-carbaldehyde；5-formyl-1,3-dimethyl-barbituric acid；5-Formyl-1,3-dimethyl-barbitursaeure；1,3-Dimethyl-2,4,6-trioxo-1,3-diazinane-5-carbaldehyde
• CAS: 42604-63-7
• 化学式: C₇H₈N₂O₄
• mdl: MFCD00219571
• 分子量: 184.152
• InChiKey: NADASDWWUUDZFH-UHFFFAOYSA-N

物化性质

• 熔点：
  182-184 °C
• 沸点：
  291.8±50.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933540000

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-2,4,6-三氧代-六氢-嘧啶-5-甲醛 在 肼 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以88%的产率得到5-[(E)-hydrazinylidenemethyl]-1,3-dimethylpyrimidine-2,4,6-trione
  参考文献：
  名称：

  Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones

  摘要：

  Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections-a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 mu M with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.010
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 在 原甲酸三乙酯 作用下， 生成 1,3-二甲基-2,4,6-三氧代-六氢-嘧啶-5-甲醛
  参考文献：
  名称：

  481. 5-氨基亚甲基-1：3-二甲基巴比妥酸

  摘要：

  DOI：

  10.1039/jr9590002401

文献信息

• Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
  作者：Branko S. Jursic、Edwin D. Stevens

  DOI：10.1016/s0040-4039(03)00111-4

  日期：2003.3

  Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate

  通过系统地研究反应条件，开发了用于获得大量取代的5-烷基和5-苄基巴比妥酸的非常有效的制备方法。该过程包括两步准备，其中第二步是还原锌粉/酸。对于制备5-烷基巴比妥酸酯，第一步是制备5-酰基或5-亚烷基巴比妥酸酯。如果5-苄基巴比妥酸酯是目标产物，则第一步包括制备5-亚苄基。无论第一步的性质如何，所有反应的合成产率均约为90％，而分离和纯化仅涉及结晶。
• Preparation of 5-formyl- and 5-acetylbarbituric acids, including the corresponding Schiff bases and phenylhydrazones
  作者：Branko S Jursic、Donna M Neumann

  DOI：10.1016/s0040-4039(01)01830-5

  日期：2001.11

  effective, and high yield synthetic procedures for formylation and acetylation of barbituric acid derivatives is described. Generated 5-acylbarbituric acids are transformed into the corresponding Schiff bases in high yield condensation reactions with ω-aminoalkanoic acids and nitrophenylhydrazines.

  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。
• [EN] COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT<br/>[FR] COMPOSITIONS, MÉTHODES D'UTILISATION ET MÉTHODES DE TRAITEMENT
  申请人：UNIV NEW ORLEANS

  公开号：WO2015048634A1

  公开（公告）日：2015-04-02

  Embodiments of the present disclosure provide for compositions including an antimicrobial agent, pharmaceutical compositions including the antimicrobial agent, methods of treatment of an infection, methods of treatment using compositions or pharmaceutical compositions, and the like.

  本公开的实施例提供了包括抗微生物剂的组合物、包括抗微生物剂的药物组合物、治疗感染的方法、使用组合物或药物组合物进行治疗的方法等。
• Copper(II) complexes with barbiturate derivatives: Synthesis, characterization and catalytic applications
  作者：Erkan Fırıncı

  DOI：10.1016/j.poly.2019.02.044

  日期：2019.5

  X-ray crystallography. The X-ray crystallographic studies revealed that complexes 3b and 3j are 2-D coordination polymers. Also, the catalytic activities of the copper(II) complexes were examined for the peroxidative oxidation of cyclohexane under mild conditions. The results showed that the yields of the oxidation products were in the range 11.3–22.1%, depending upon the complex used and the promoter

  摘要由5-甲酰基巴比妥酸酯与伯芳基胺反应制备了巴比妥酸酯衍生物。通过用制备的巴比妥酸酯衍生物处理乙酸铜（II）一水合物来合成相应的铜（II）配合物。所有新化合物均通过元素分析和光谱法进行了表征。用X射线晶体学测定3b和3j的结构。X射线晶体学研究表明，络合物3b和3j是2-D配位聚合物。同样，在温和条件下，研究了铜（II）配合物的催化活性对环己烷的过氧化氧化作用。结果表明，取决于所用的配合物和助催化剂，氧化产物的产率在11.3-22.1％的范围内。
• Pyrimidine-2,4,6-trione copper(II) complexes and their catalytic activities in the peroxidative oxidation of cyclohexane
  作者：Erkan Fırıncı

  DOI：10.1016/j.molstruc.2019.05.009

  日期：2019.10

  analysis and ATR-FTIR spectroscopy. Also, the molecular structures of 3b and 3f were determined by single crystal X-ray diffraction technique. 3b is six coordinated copper(II) complex and the geometry around Cu(II) is distorted elongated octahedral coordination while 3f is four coordinated copper(II) complex and the Cu(II) atom has a perfect square planar geometry. Furthermore, the synthesized Cu(II) complexes

  摘要 5-[(N-芳基氨基)-亚甲基]嘧啶-2,4,6-三酮衍生物由N-芳胺衍生物与5-甲酰基-嘧啶-2,4,6-三酮衍生物反应制备，并表征为元素分析、ATR-FTIR、1H 和 13C NMR 光谱。Cu(II) 配合物是通过两当量的嘧啶-2,4,6-三酮配体与一当量的 Cu(OAc)2.H2O 反应合成的，并通过元素分析和 ATR-FTIR 光谱表征。此外，3b和3f的分子结构是通过单晶X射线衍射技术确定的。3b 是六配位的铜（II）配合物，Cu（II）周围的几何形状是扭曲拉长的八面体配位，而 3f 是四配位的铜（II）配合物，Cu（II）原子具有完美的方形平面几何形状。此外，