(5-methyl-2,4-dioxo-1H,3H-pyrimidin-1-yl)acetohydrazide | 1000071-56-6

• 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-methyl-2,4-dioxo-1H,3H-pyrimidin-1-yl)acetohydrazide
• 英文别名: 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetohydrazide；2-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetohydrazide；2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetohydrazide
• CAS: 1000071-56-6
• 化学式: C₇H₁₀N₄O₃
• 分子量: 198.181
• InChiKey: NBVHCQNPCVDWLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: ethanol (64-17-5))
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-methyl-2,4-dioxo-1H,3H-pyrimidin-1-yl)acetohydrazide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-cyclohexyl-3,5-dimethyl-N'-(2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl)benzohydrazide
  参考文献：
  名称：

  Design and synthesis of N-alkyl-N′-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist

  摘要：

  Based on the discovery of thymine as an ecdysteroid agonist, a series of 1,4-disubstituted diacylhydrazine derivatives with a thymine moiety were designed and synthesized. The activities of these compounds against Spodoptera litura (Fabricius) were evaluated by the insect immersion method. Results showed that compound 2h with an N-cyclohexylmethyl substituent exhibits the most potent agonist activity with a median lethal concentration of 23.21 mu g/mL. This compound also caused malformation of molting larvae and adults. Compound 2h was further demonstrated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). A molecular docking study indicated that hydrophobic interactions and the formation of hydrogen bonds between the compounds and the ecdysone receptor play critical roles in promoting the binding affinity of the compound. The structure of compound 2h may serve as a favorable template for the development of new ecdysteroid agonists with a pyrimidinedione moiety. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.010
• 作为产物：
  描述：

  1-(ethoxycarbonylmethyl)thymine 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以93%的产率得到(5-methyl-2,4-dioxo-1H,3H-pyrimidin-1-yl)acetohydrazide
  参考文献：
  名称：

  糖尿嘧啶-1-基甲基腙及其恶二唑啉衍生物的合成及抗病毒评价

  摘要：

  已合成 1-Carbethoxymethyluracils 并衍生为相应的酰肼，其与单糖反应得到相应的糖腙。后者在吡啶中用乙酸酐乙酰化，得到过-O-乙酰基衍生物，而在乙酸酐中加热得到相应的恶二唑啉。测试了制备的化合物对乙型肝炎病毒的抗病毒活性，并显示出中等活性。

  DOI：

  10.1055/s-2007-983878

文献信息

• Synthesis of Components for the Generation of Constitutional Dynamic Analogues of Nucleic Acids
  作者：David T. Hickman、Nampally Sreenivasachary、Jean-Marie Lehn

  DOI：10.1002/hlca.200890022

  日期：2008.1

  medium, template), would provide an alternative approach to the de novo design of functional dynamic bio-macromolecules. As a first step towards this goal, various mono- and bifunctionalised (hetero- and homotopic) nucleic acid-derived building blocks of type I–X have been synthesised for the generation of dynamic main-chain and side-chain reversible nucleic acid analogues. Hydrazide- and/or acetal

  动态共价聚合物的引入（其中单体单元通过可逆共价键连接并且可以进行组分交换）为功能材料的产生开辟了新的可能性。将这种方法扩展到能够在水介质中生成动态生物聚合物的过程中，能够使构造（序列，长度）适应外部因素（例如环境，介质，模板），这将为功能动力学的从头设计提供一种替代方法。生物大分子。作为朝着这个目标迈出的第一步，各种I - X型单官能和双官能（异位和同位）核酸衍生构件已经合成了用于产生动态主链和侧链可逆核酸类似物的化合物。选择了由酰肼和/或乙缩醛（受保护的羰基）官能化的组分，它们在柔韧性，长度，净形式电荷和酰肼/缩醛取代基方面有所不同，以探讨这些因素如何影响性能（结构，溶解度） ，分子识别特征）可能由缩聚产生的聚合物产物。
• Synthesis and Antiviral Evaluation of Sugar Uracil-1-ylmethylhydrazones and Their Oxadiazoline Derivatives
  作者：Omar Ali、Adel Abdel-Rahman、Hamada Amer

  DOI：10.1055/s-2007-983878

  日期：2007.9

  hydrazides, which were reacted with monosaccharides to afford the corresponding sugar hydrazones. Acetylation of the latter with acetic anhydride in pyridine, afforded the per- O-acetyl derivatives, while heating in acetic anhydride gave the corresponding oxadiazolines. The prepared compounds were tested for antiviral activity against hepatitis B virus and showed moderate activities.

  已合成 1-Carbethoxymethyluracils 并衍生为相应的酰肼，其与单糖反应得到相应的糖腙。后者在吡啶中用乙酸酐乙酰化，得到过-O-乙酰基衍生物，而在乙酸酐中加热得到相应的恶二唑啉。测试了制备的化合物对乙型肝炎病毒的抗病毒活性，并显示出中等活性。
• Design and synthesis of N-alkyl-N′-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist
  作者：Xiu Liu、Ling Zhang、Jin-Guo Tan、Han-Hong Xu

  DOI：10.1016/j.bmc.2013.05.010

  日期：2013.8

  Based on the discovery of thymine as an ecdysteroid agonist, a series of 1,4-disubstituted diacylhydrazine derivatives with a thymine moiety were designed and synthesized. The activities of these compounds against Spodoptera litura (Fabricius) were evaluated by the insect immersion method. Results showed that compound 2h with an N-cyclohexylmethyl substituent exhibits the most potent agonist activity with a median lethal concentration of 23.21 mu g/mL. This compound also caused malformation of molting larvae and adults. Compound 2h was further demonstrated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). A molecular docking study indicated that hydrophobic interactions and the formation of hydrogen bonds between the compounds and the ecdysone receptor play critical roles in promoting the binding affinity of the compound. The structure of compound 2h may serve as a favorable template for the development of new ecdysteroid agonists with a pyrimidinedione moiety. (C) 2013 Elsevier Ltd. All rights reserved.