5-benzoyl-pyrimidine-2,4,6-trione | 91135-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoyl-pyrimidine-2,4,6-trione
• 英文别名: 5-benzoyl-1,3-diazinane-2,4,6-trione
• CAS: 91135-71-6
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: SCNVVYSDQBAFDE-UHFFFAOYSA-N

物化性质

• 熔点：
  275 °C
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzoyl-pyrimidine-2,4,6-trione 在 一水合肼 、 溶剂黄146 作用下， 生成 5-(α-hydrazono-benzyl)-barbituric acid
  参考文献：
  名称：

  Biltz; Koehler, Chemische Berichte, 1923, vol. 56, p. 2487

  摘要：

  DOI：
• 作为产物：
  描述：

  巴比妥酸 、 苯甲酰氯 在 吡啶 作用下， 反应 2.0h， 以90%的产率得到5-benzoyl-pyrimidine-2,4,6-trione
  参考文献：
  名称：

  简单，高效，高产率的取代和未取代的5-苯甲酰基巴比妥酸及其相应席夫碱苯基hydr的合成

  摘要：

  介绍了生物学上重要的苯甲酰基巴比妥酸酯的制备方法。优化了几种程序以涵盖各种取代的5-苯甲酰基巴比妥酸酯的制备。为了进一步探讨这些化合物的生物学重要性，讨论了苯甲酰基巴比妥酸酯及其对应盐与有机胺的硝基苯基-的多克制备方法。已经证明这些化合物可以几种互变异构形式存在，并且溶液中的平衡可以通过温度以及溶液的pH来改变。对苯甲酰基巴比妥酸酯的硝基苯基hydr进行的X射线结构分析与所提出的光谱研究完全吻合。AMI半经验研究表明，在苯甲酰基巴比妥酸酯的气相中，烯醇形式优于酮形式，这也通过以氯仿为溶剂的NMR光谱研究得到了证实。此外，与X射线确定的结构相比，AMI计算了4-羟基苯甲酰基巴比妥酸酯的二硝基苯基hydr的结构和电子性质。

  DOI：

  10.1002/jhet.5570410214

文献信息

• [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。
• COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT
  申请人：THE UNIVERSITY OF NEW ORLEANS

  公开号：US20160235752A1

  公开（公告）日：2016-08-18

  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的治疗方法等。
• Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
  作者：Donna M. Neumann、Amy Cammarata、Gregory Backes、Glen E. Palmer、Branko S. Jursic

  DOI：10.1016/j.bmc.2013.12.010

  日期：2014.1

  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.
• Simple, efficient, high yield syntheses of substituted and unsubstituted 5-benzoylbarbituric acids, and their corresponding schiff base phenylhydrazones
  作者：Branko S. Jursic、Donna M. Neumann、Katharine L. Bowdy、Edwin D. Stevens

  DOI：10.1002/jhet.5570410214

  日期：2004.3

  several tautomeric forms and that the equilibrium in solution can be changed by temperature as well as by the pH of the solution. X-ray structural analysis performed on one of the nitrophenylhydrazones of benzoylbarbiturates fully agrees with the presented spectroscopic studies. AMI semi-empirical studies show that the enol form is preferred in the gas phase of benzoylbarbiturates over the keto form,

  介绍了生物学上重要的苯甲酰基巴比妥酸酯的制备方法。优化了几种程序以涵盖各种取代的5-苯甲酰基巴比妥酸酯的制备。为了进一步探讨这些化合物的生物学重要性，讨论了苯甲酰基巴比妥酸酯及其对应盐与有机胺的硝基苯基-的多克制备方法。已经证明这些化合物可以几种互变异构形式存在，并且溶液中的平衡可以通过温度以及溶液的pH来改变。对苯甲酰基巴比妥酸酯的硝基苯基hydr进行的X射线结构分析与所提出的光谱研究完全吻合。AMI半经验研究表明，在苯甲酰基巴比妥酸酯的气相中，烯醇形式优于酮形式，这也通过以氯仿为溶剂的NMR光谱研究得到了证实。此外，与X射线确定的结构相比，AMI计算了4-羟基苯甲酰基巴比妥酸酯的二硝基苯基hydr的结构和电子性质。
• Biltz; Koehler, Chemische Berichte, 1923, vol. 56, p. 2487
  作者：Biltz、Koehler

  DOI：——

  日期：——

表征谱图