5,5-二苄基巴比妥酸 | 26371-47-1

• 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: 5,5-二苄基巴比妥酸
• 英文名称: 5,5-dibenzyl-2,3,4(1H,3H,5H)pyrimidinetrione
• 英文别名: 5,5-dibenzyl-barbituric acid；dibenzylbarbital；5,5-Dibenzyl-barbitursaeure；5,5-dibenzyl-pyrimidine-2,4,6-trione；Barbituric acid, 5,5-dibenzyl-；5,5-dibenzyl-1,3-diazinane-2,4,6-trione
• CAS: 26371-47-1
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: SLCFHAGEVYERLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933540000

反应信息

• 作为反应物：
  描述：

  5,5-二苄基巴比妥酸 在 sodium hydroxide 作用下， 生成 2,2-dibenzyl-N-carbamoyl-malonamic acid
  参考文献：
  名称：

  Aspelund, Acta Academiae Aboensis, Series B: Mathematica et Physica, 1955, vol. 20, # 3, p. 5

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 mineral acid 作用下， 生成 5,5-二苄基巴比妥酸
  参考文献：
  名称：

  Conrad, Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 312

  摘要：

  DOI：

文献信息

• Single-component, low molecular weight organic supergelators based on chiral barbiturate scaffolds
  作者：Daniel T. Seidenkranz、Kurt A. Langworthy、Lev N. Zakharov、Michael D. Pluth

  DOI：10.1080/10610278.2019.1629437

  日期：2019.8.3

  ABSTRACT We report here the first chiral barbiturate to act as a single-component LMOG capable of gelating a variety of chlorinated and aromatic solvents. Solution-based DOSY NMR experiments, solid-state VP-SEM, and X-ray crystallography techniques were used to characterize chloroform-based gels at a variety of size domains. This scaffold provides a simple system to study the dynamics of gelation and

  摘要 我们在此报告了第一种手性巴比妥酸盐作为单组分 LMOG，能够胶凝各种氯化和芳香溶剂。基于溶液的 DOSY NMR 实验、固态 VP-SEM 和 X 射线晶体学技术用于表征各种尺寸域的基于氯仿的凝胶。该支架提供了一个简单的系统来研究凝胶化和自组装的动力学。图形概要
• Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
  作者：Branko S Jursic、Donna M Neumann

  DOI：10.1016/s0040-4039(01)00621-9

  日期：2001.6

  Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).

  有效的单-和二-制备合成程序Ç通过钯和巴比土酸溶液的铂催化氢化烷基化巴比土酸衍生物（未取代的，Ñ -单和Ñ，N'二取代的巴比土酸）和羰基化合物（脂族和芳族醛和酮）。
• Preparation of 5-substituted benzylbarburituric acids and investigation of the effect of the benzyl and substituted benzyl groups on the acidity of barbituric acid
  作者：John V. Tate、William N. Tinnerman、Vito Jurevics、Harold Jeskey、Edward R. Biehl

  DOI：10.1002/jhet.5570230103

  日期：1986.1

  5-substituted benzylbarbituric acids has been determined in 50% ethanol/water and they were found to be more acidic than barbituric acid. The pKas of these derivatives obey Hammett's equation indicating that their acidity is affected by substituents in the same manner as the benzoic acid ionization constants. A synthesis of these acids is described.

  已在50％的乙醇/水中测定了5-苄基巴比妥酸和一系列5-取代的苄基巴比妥酸的酸度，发现它们比巴比妥酸更酸性。这些衍生物的p K a s服从哈米特方程，表明它们的酸度受取代基影响的方式与苯甲酸电离常数相同。描述了这些酸的合成。
• Fluorescent Arylethynyl Hamilton Receptors for Barbiturate Sensing
  作者：Daniel T. Seidenkranz、Michael D. Pluth

  DOI：10.1021/acs.joc.9b00978

  日期：2019.7.5

  Barbiturates are common targets for molecular recognition in preorganized receptors due to complementary hydrogen-bond donor/acceptor interactions. Although many such receptors exhibit high selectivity and affinity for barbiturate guests, relatively few of these systems have desirable photophysical properties for sensing applications. Here, we report the synthesis, optoelectronic properties, and binding

  由于互补的氢键供体/受体相互作用，巴比妥类化合物是在预组织受体中进行分子识别的常见靶标。尽管许多这样的受体对巴比妥类客人表现出高选择性和亲和力，但是这些系统中相对很少的具有传感应用所需的光物理性质。在这里，我们报告了一组荧光芳基乙炔基汉密尔顿受体的合成，光电性能和结合亲和力。我们还提供了对这些系统进行高效荧光设计以用作荧光巴比妥酸盐传感器所需的设计原理的见解。
• 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.