5-(4-{[4,6-dioxo-2-thioxotetrahydro-5(2H)-pyrimidinylidene]methyl}-benzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione | 23193-24-0

• 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-(4-{[4,6-dioxo-2-thioxotetrahydro-5(2H)-pyrimidinylidene]methyl}-benzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
• 英文别名: 5-(4-((tetrahydro-4,6-dioxo-2-thiopyrimidin-5(6H)-ylidene)methyl)benzylidene)dihydro-2-thiooxopyrimidine-4,6(1H,3H)-dione；5,5'-(1,4-phenylenebis(methanylylidene))bis(2-thioxodihydropyrimidine-4,6(1H,5H)-dione)；2,2'-dithioxo-tetrahydro-5,5'-(p-phenylene-dimethylene)-bis-pyrimidine-4,6-dione；5,5'-(p-Phenylendimethylidin)-bis (2-thiobarbitursaeure)；5-[[4-[(4,6-Dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)methyl]phenyl]methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 23193-24-0
• 化学式: C₁₆H₁₀N₄O₄S₂
• 分子量: 386.412
• InChiKey: XCWNXFLFZLFHAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 对苯二甲醛 在 deep eutectic solvent 作用下， 反应 2.0h， 以95%的产率得到5-(4-{[4,6-dioxo-2-thioxotetrahydro-5(2H)-pyrimidinylidene]methyl}-benzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
  参考文献：
  名称：

  通过更环保的方法合成一些新型嘧啶二酮和嘧啶三酮衍生物：研究它们的抗菌活性和光物理特性

  摘要：

  摘要 通过不同的技术合成了一系列基于嘧啶二酮和嘧啶三酮的新型化合物，例如单独使用常规 Knoevenagel 缩合、使用米根霉脂肪酶生物催化剂和使用深共熔溶剂 (DES)。发现使用脂肪酶和 DES 的产量最大。脂肪酶和 DES 的重复使用最多可达四个连续循环。这些方法温和、高效且易于放大。发现这些产品在体外对大肠杆菌、肺炎假单胞菌和微球菌具有显着的抗菌活性，对黑曲霉和白色念珠菌具有体外抗真菌活性。所有化合物对受试菌株均表现出可观的体外活性。还研究了产物的光物理性质和热稳定性。图形概要

  DOI：

  10.1080/00397911.2011.611324

文献信息

• Verjuice as a green and bio-degradable solvent/catalyst for facile and eco-friendly synthesis of 5-arylmethylenepyrimidine-2,4,6-trione, pyrano[2,3-d]pyrimidinone and pyrimido[4,5-d]pyrimidinone derivatives
  作者：Niloufar Safari、Farhad Shirini、Hassan Tajik

  DOI：10.1007/s13738-018-1565-y

  日期：2019.4

  of the synthesis of 5-arylmethylenepyrimidine-2,4,6-triones, via Knovenagel condensation reaction between barbituric or thiobarbituric acid and aldehydes. Verjuice is also employed for the effective synthesis of pyrano[2,3-d]pyrimidinone derivatives via a three-component reaction of barbituric acid or its thio analogue, aldehydes and malononitrile. In the same way, pyrimido[4,5-d]pyrimidinone derivatives

  Verjuice（未成熟的葡萄汁）是一种有机酸的天然混合物，可通过pH值和TGA分析鉴定，可通过Knovenagel缩合有效地用于促进5-芳基亚甲基嘧啶-2,4,6-三酮的合成。巴比妥酸或硫代巴比妥酸与醛之间的反应。Verjuice还用于通过巴比妥酸或其硫代类似物，醛和丙二腈的三组分反应有效合成吡喃并[2,3- d ]嘧啶酮衍生物。同样，嘧啶基[4,5- d]嘧啶酮衍生物可简单地通过巴比妥酸，醛与脲或硫脲在果汁中的反应来制备。这种绿色方法学具有显着的优势，包括操作简单，可接受的反应时间，易于后处理，高收率，避免在反应和后处理过程中使用任何昂贵的起始原料，挥发性和有害有机溶剂以及使用天然，低成本，可重复使用且可生物降解的催化剂。
• Sulfuric acid-modified PEG-6000 (PEG–OSO3H): a biodegradable, reusable solid acid catalyst for highly efficient and eco-friendly synthesis of novel bis-Knoevenagel products under solvent-free conditions
  作者：Zeba N. Siddiqui、Tabassum Khan

  DOI：10.1016/j.tetlet.2013.05.012

  日期：2013.7

  PEG-6000 (PEG–OSO3H) is used as a highly efficient, biodegradable, and reusable acid catalyst for the synthesis of novel acyclic and heterocyclic bis-Knoevenagel products under thermal solvent-free conditions. The remarkable features of this green, new methodology are high conversions, cleaner reaction profile, simple experimental and work-up procedure, and economic viability. The catalyst is characterized

  硫酸改性的PEG-6000（PEG-OSO 3 H）被用作高效，可生物降解和可重复使用的酸催化剂，用于在无热溶剂的条件下合成新型无环和杂环双-Knoevenagel产品。这种绿色的新方法的显着特点是高转化率，更清洁的反应曲线，简单的实验和后处理程序以及经济可行性。首次通过SEM-EDX和粉末XRD对催化剂进行了表征。催化剂可以重复使用几次，而不会显着降低其催化活性。
• Synthesis and structure–activity relationship of thiobarbituric acid derivatives as potent inhibitors of urease
  作者：Khalid Mohammed Khan、Fazal Rahim、Ajmal Khan、Muhammad Shabeer、Shafqat Hussain、Wajid Rehman、Muhammad Taha、Momin Khan、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2014.05.057

  日期：2014.8

  A series of thiobarbituric acid derivatives 1-27 were synthesized and evaluated for their urease inhibitory potential. Exciting results were obtained from the screening of these compounds 1-27. Compounds 5, 7, 8, 11, 16, 17, 22, 23 and 24 showed excellent urease inhibition with IC50 values 18.1 ± 0.52, 16.0 ± 0.45, 16.0 ± 0.22, 14.3 ± 0.27, 6.7 ± 0.27, 10.6 ± 0.17, 19.2 ± 0.29, 18.2 ± 0.76 and 1.61 ± 0.18 μM, respectively, much better than the standard urease inhibitor thiourea (IC₅₀=21 ± 0.11 μM). Compound 3, 4, 10, and 26 exhibited comparable activities to the standard with IC₅₀ values 21.4 ± 1.04 and 21.5 ± 0.61 μM, 22.8 ± 0.32, 25.2 ± 0.63, respectively. However the remaining compounds also showed prominent inhibitory potential The structure-activity relationship was established for these compounds. This study identified a novel class of urease inhibitors. The structures of all compounds were confirmed through spectroscopic techniques such as EI-MS and (1)H NMR.