5-acetyl-1-phenyl-pyrimidine-2,4,6-trione | 91974-06-0

• 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-acetyl-1-phenyl-pyrimidine-2,4,6-trione
• 英文别名: 5-acetyl-1-phenyl-barbituric acid；5-Acetyl-1-phenyl-barbitursaeure；1-Phenyl-5-acetyl-barbitursaeure；5-Acetyl-1-phenyl-1,3-diazinane-2,4,6-trione
• CAS: 91974-06-0
• 化学式: C₁₂H₁₀N₂O₄
• 分子量: 246.222
• InChiKey: QRFZVXIQSQOFMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-acetyl-1-phenyl-pyrimidine-2,4,6-trione 、 4-硝基苯肼 以 甲醇 为溶剂， 反应 2.0h， 生成
  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：

  苯基脲 在 盐酸 、 乙醇 、 sodium ethanolate 作用下， 生成 5-acetyl-1-phenyl-pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Ridi, Annali di Chimica, 1952, vol. 42, p. 25,29

  摘要：

  DOI：

文献信息

• 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。
• US4260776A
  申请人：——

  公开号：US4260776A

  公开（公告）日：1981-04-07
• 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.
• Ridi, Annali di Chimica, 1952, vol. 42, p. 25,29
  作者：Ridi

  DOI：——

  日期：——

表征谱图