5-[(4-nitrophenyl)hydrazono]pyrimidine-2,4,6-trione | 19849-55-9

• 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: 5-[(4-nitrophenyl)hydrazono]pyrimidine-2,4,6-trione
• 英文别名: pyrimidinetetraone 5-[(4-nitro-phenyl)-hydrazone]；alloxan-5-(4-nitro-phenylhydrazone)；Alloxan-5-(4-nitro-phenylhydrazon)；5-[(4-nitrophenyl)hydrazinylidene]-1,3-diazinane-2,4,6-trione
• CAS: 19849-55-9
• 化学式: C₁₀H₇N₅O₅
• mdl: MFCD00596775
• 分子量: 277.196
• InChiKey: JPJTXLMEYXEHES-UHFFFAOYSA-N

物化性质

• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142.8
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-[(4-nitrophenyl)hydrazono]pyrimidine-2,4,6-trione 、 alkaline earth salt of/the/ methylsulfuric acid 生成 [(4-nitro-phenylhydrazono)-acetyl]-carbamic acid
  参考文献：
  名称：

  Kuehling, Chemische Berichte, 1898, vol. 31, p. 1973

  摘要：

  DOI：
• 作为产物：
  描述：

  巴比妥酸 、 4-硝基氯化重氮苯 在 盐酸 作用下， 生成 5-[(4-nitrophenyl)hydrazono]pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Kuehling, Chemische Berichte, 1898, vol. 31, p. 1973

  摘要：

  DOI：

文献信息

• Preparation and hydrogen bonding studies of phenylhydrazone derivatives of alloxan: crystal and molecular structure of pyrimidine-2(1H),4(3H),5,6-tetraone 5-(2-nitrophenyl)hydrazone
  作者：Haydn G. Beaton、Gerald R. Willey、Michael G. B. Drew

  DOI：10.1039/p29870000469

  日期：——

  Eight phenylhydrazone derivatives of pyrimidine-2(1H),4(3H),5,6-tetraone, or 5-oxobarbituric acid (alloxan), are described. Spectroscopic pyrimidine (1H n.m.r., i.r.) data indicate the presence of extensive hydrogen bonding which, as shown by X-ray crystallographic data for the title hydrazone, includes both intra- and inter-molecular interactions. The title hydrazone, C10H7N5O5, is monoclinic, space

  描述了嘧啶-2（1 H），4（3 H），5,6-四酮或5-氧代巴比妥酸（四氧六环）的八种苯hydr衍生物。嘧啶光谱（1 H nmr，ir）数据表明存在广泛的氢键，如标题的X射线晶体学数据所示，该氢键包括分子内和分子间相互作用。标题C 10 H 7 N 5 O 5为单斜晶，空间群P 2 1 / a，a = 9.104（8），b = 17.975（13），c = 10.333（8）Å，β= 113.5（ 1）°，Z = 4.2145已在衍射仪上测量了独立反射，并通过直接方法确定了结构，并将其精炼为R 0.074。在不对称单元中有四个独立的氢键：两个分子内键将N（7）–H（7）连接到苯环的o -NO 2基团和巴比妥酸酯环的羰基上，两个分子间键连接通过对称中心将巴比妥酸酯环的NH位点连接至溶剂NN-二甲基甲酰胺氧原子和另一个巴比妥酸酯环的羰基氧原子。
• 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.
• Coordination compounds of some d metals with nitrophenylhydrazone oxopyridine (pyrimidine) derivatives: Crystal and molecular structure of C10H9N5O6
  作者：O. V. Kovalchukova、A. V. Churakov、S. B. Strashnova、Al-Tahan Rana Abdulillah Abbas、V. S. Sergienko、D. N. Kuznetsov、K. I. Kobrakov

  DOI：10.1134/s0036023613040086

  日期：2013.4

  Twelve new d-metal complexes with 5-[(4-nitrophenyl)hydrazo]pyrimidine-2,4,6-trione (HL1) and 4-methyl-5-[4-nitrophenylhydrazo]-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitryl (HL2) have been synthesized and separated out in the crystalline state. The crystal and molecular structures of HL1 have been solved by X-ray diffraction analysis. The organic molecule exists in the crystalline state as a planar hydrazo tautomer stabilized by intramolecular hydrogen bonds. Metal coordination is bidentate chelate. The acid-base equilibria and complexation of the ligands in solutions have been studied, and the complexation constants have been found.
• Kuehling, Chemische Berichte, 1898, vol. 31, p. 1973
  作者：Kuehling

  DOI：——

  日期：——