1,3-dimethyl-5-(phenylazo)barbituric acid | 30189-12-9

• 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: 1,3-dimethyl-5-(phenylazo)barbituric acid
• 英文别名: dimethyl-pyrimidinetetraone 5-phenylhydrazone；dimethyl-alloxan-5-phenylhydrazone；Dimethyl-alloxan-5-phenylhydrazon；1,3-Dimethyl-5-(phenylhydrazono)-alloxan；1,3-Dimethyl-5-phenylhydrazon-alloxan；1,3-dimethyl-5-(phenylhydrazinylidene)-1,3-diazinane-2,4,6-trione
• CAS: 30189-12-9
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: DQNOMULJOAQRJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82.08
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-(phenylazo)barbituric acid 、 甲氧羰基亚甲基三苯基正膦 以 甲苯 为溶剂， 反应 10.0h， 以73%的产率得到5,7-Dimethyl-2-phenyl-2H,5H-pyrimido[5,4-c]pyridazine-3,6,8-trione
  参考文献：
  名称：

  Nada, Afaf Aly; Erian, Ayman Wahba; Mohamed, Nadia Ragab, Journal of Chemical Research, Miniprint, 1997, # 7, p. 1576 - 1594

  摘要：

  DOI：
• 作为产物：
  描述：

  6-amino-1,3-dimethyl-5-phenylazouracilate 在 吡啶 作用下， 生成 1,3-dimethyl-5-(phenylazo)barbituric acid
  参考文献：
  名称：

  Ishidate et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1107

  摘要：

  DOI：

文献信息

• Conversion of 1,3-Dimethyl-5-(Arylazo)-6-Amino-Uracils to 1,3-Dimethyl-5-(Arylazo)-Barbituric Acids: Spectroscopic Characterization, Photophysical Property and Determination of pK_aof the Products
  作者：Diptanu Debnath、Atanu Purkayastha、Rupasree Choudhury、Tarun Kumar Misra

  DOI：10.1002/jccs.201600007

  日期：2016.7

  The study of inter‐conversion between molecules, especially biologically and pharmaceutically important molecules, is extremely important. This study reports the inter‐conversion between two azo‐derivtives: azo‐6‐aminouracils to azo‐barbituric acids. We successfully converted the 1,3‐dimethyl‐5‐(arylazo)‐6‐aminouracils (Uazo‐1 to Uazo‐4) to 1,3‐dimethyl‐5‐(arylazo)‐barbituric acids (BAazo‐1 to BAazo‐4)

  分子之间，尤其是生物学上和药学上重要的分子之间的相互转化研究非常重要。这项研究报告了两种偶氮衍生物之间的相互转化：偶氮6-氨基尿嘧啶向偶氮巴比妥酸。我们成功地将1,3-二甲基-5-（芳基偶氮）-6-氨基尿嘧啶（Uazo-1转化为Uazo-4）转化为1,3-二甲基-5（芳基偶氮）-巴比妥酸（BAazo-1转化为BAazo- 4）（其中，aryl⇒C 6 ħ 5 - （1）; p -MeC 6 ħ 4 - （2），p -ClC 6 ħ 4 - （3）和p‐ NO 2 C 6 H 4‐（4））遵循酸水解路径。使用紫外可见光谱，红外光谱和核磁共振光谱仪等光谱仪对产品进行表征。所制备染料的紫外可见光谱表明，与偶氮-6-氨基尿嘧啶相比，它们几乎对溶剂合变色反应不灵敏。制备的偶氮巴比妥酸的红外光谱表现出三个>CO的特征频率，而不是偶氮6-6氨基尿嘧啶的两个特征频率。1个反映溶液种类存在的1 H NMR
• Visible light mediated organocatalytic dehydrogenative aza-coupling of 1,3-diones using aryldiazonium salts
  作者：Ramanand Das、Taraknath Kundu、Joneswar Basumatary

  DOI：10.1039/d2ra07807d

  日期：——

  An efficient protocol for diazenylation of 1,3-diones under photoredox conditions is presented herein. C–N bond forming Csp3–H functionalization of cyclic and alkyl diones by unstable aryl diazenyl radicals is achieved through reaction with aryldiazonium tetrafluoroborates by organocatalysts under visible light irradiation. The reaction has wide substrate scope, gives excellent yields, and is also

  本文提出了在光氧化还原条件下 1,3-二酮二氮烯基化的有效方案。在有机催化剂的可见光照射下，不稳定的芳基二氮烯基自由基与芳基重氮四氟硼酸盐反应，实现了环二酮和烷基二酮的 C-N 键形成 C sp 3 -H 官能化。该反应底物范围广，产率优异，并且在水作为绿色溶剂中也很有效。该方法提供了一种容易获得芳基二氮烯基衍生物的方法，芳基二氮烯基衍生物是合成氮杂杂环以及潜在药效团的有用关键起始材料。
• Synthesis, activity evaluation, and docking analysis of barbituric acid aryl hydrazone derivatives as RSK2 inhibitors
  作者：Mengzhu Xue、Minghao Xu、Weiqiang Lu、Jin Huang、Honglin Li、Yufang Xu、Xiaofeng Liu、Zhenjiang Zhao

  DOI：10.3109/14756366.2012.681651

  日期：2013.8.1

  The 90 kDa ribosomal S6 kinases (RSKs), especially RSK2, have attracted attention for the development of new anticancer agents. Through structural optimization of the hit compound 1 from our previous study, a series of barbituric acid aryl hydrazone analogues were designed and synthesized as potential RSK2 inhibitors. The most potent one, compound 9, showed a higher activity against RSK2 with an IC50 value of 1.95 mu M. To analyze and elucidate their structure-activity relationship, the homology model of RSK2 N-terminal kinase domain was built and molecular docking simulations were performed, which provide helpful clues to design new inhibitors with desired activities.
• Kuehling, Chemische Berichte, 1891, vol. 24, p. 4141
  作者：Kuehling

  DOI：——

  日期：——
• SAKAMOTO T.; TERAO Y.; SEKIYA M., CHEM. AND PHARM. BULL. <CPBT-AL>, 1977, 25, NO 4, 731-739
  作者：SAKAMOTO T.、 TERAO Y.、 SEKIYA M.

  DOI：——

  日期：——