5-(4-nitrobenzyl)-1,3-dimethylbarbituric acid | 182955-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-nitrobenzyl)-1,3-dimethylbarbituric acid
• 英文别名: 1,3-Dimethyl-5-(4-nitrobenzoyl)-1,3-diazinane-2,4,6-trione
• CAS: 182955-15-3
• 化学式: C₁₃H₁₁N₃O₆
• 分子量: 305.247
• InChiKey: GYUWWUXRXWPPPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-nitrobenzyl)-1,3-dimethylbarbituric acid 在 sodium azide 、 五氯化磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.0h， 生成 5,7-Dimethyl-3-(4-nitro-phenyl)-7H-isoxazolo[5,4-d]pyrimidine-4,6-dione
  参考文献：
  名称：

  azidouracils对oxazolo-和isoxazolopyrimidines的闭环反应†

  摘要：

  在多磷酸存在下对6-azidouracils 1的热解会生成恶唑并[5,4- d ]嘧啶-5,7-二酮5（通过与苯甲酸2a反应）或异恶唑并[3,4- d ]嘧啶-4，6-二酮7（通过与脂族羧酸2b，c反应）。通过用五氯化磷氯化并随后与叠氮化钠反应，可以显示5-苯甲酰基嘧啶三酮12环化成异恶唑并[5,4 - d ]嘧啶-4,6-二酮15。

  DOI：

  10.1002/jhet.5570330404
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 4-硝基苯甲酰氯 在 sodium hydroxide 作用下， 生成 5-(4-nitrobenzyl)-1,3-dimethylbarbituric acid
  参考文献：
  名称：

  azidouracils对oxazolo-和isoxazolopyrimidines的闭环反应†

  摘要：

  在多磷酸存在下对6-azidouracils 1的热解会生成恶唑并[5,4- d ]嘧啶-5,7-二酮5（通过与苯甲酸2a反应）或异恶唑并[3,4- d ]嘧啶-4，6-二酮7（通过与脂族羧酸2b，c反应）。通过用五氯化磷氯化并随后与叠氮化钠反应，可以显示5-苯甲酰基嘧啶三酮12环化成异恶唑并[5,4 - d ]嘧啶-4,6-二酮15。

  DOI：

  10.1002/jhet.5570330404

文献信息

• 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。
• 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.