(4-Amino-2-oxido-1,2,5-oxadiazol-2-ium-3-yl)-morpholin-4-ylmethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (4-Amino-2-oxido-1,2,5-oxadiazol-2-ium-3-yl)-morpholin-4-ylmethanone
• 化学式: C₇H₁₀N₄O₄
• 分子量: 214.181
• InChiKey: AKHQQCRSOIRCGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-Amino-2-oxido-1,2,5-oxadiazol-2-ium-3-yl)-morpholin-4-ylmethanone 在 nitrosonium tetrafluoroborate 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 三氟乙酸 为溶剂， 生成 3-(morpholine-4-carbonyl)-4-(5-oxido-1,2,3,4-oxatriazol-3-ium-3-yl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Antiaggregant effects of (1,2,5‐oxadiazolyl)azasydnone ring assemblies as novel antiplatelet agents

  摘要：

  AbstractA series of biheterocyclic assemblies comprising of 1,2,5‐oxadiazole and azasydnone scaffolds were synthesized and biologically evaluated as novel nitric oxide (NO)‐donor and antiplatelet agents. Depending on functional substituents at the biheterocyclic core, all studied compounds demonstrated good NO‐donor profiles releasing NO in a wide range of concentrations (19.2%–195.1%) according to a Griess assay. (1,2,5‐Oxadiazolyl)azasydnones showed excellent antiplatelet activity in the case of ADP and adrenaline used as inducers completely suppressing the aggregate formation even at the lowest test concentration of 0.0375 μmol/ml, which is a rather unique feature. Moreover, studied biheterocycles possess a selective mechanism of inhibition of platelet aggregation mediated only by ADP and adrenaline, which are considered to be the main inducers causing thrombus formation. In addition, (1,2,5‐oxadiazolyl)azasydnones were found to be completely non‐toxic to hybrid endothelial cells EaHy 926. Studies of hydrolytic degradation of the synthesized compounds afforded benzoic acid as a sole detectable decomposition product, which is considered advantageous in drug design. Therefore, (1,2,5‐oxadiazolyl)azasydnones represent a novel class of promising drug candidates with improved antiplatelet profile and reduced toxicity enabling their huge potential in medicinal chemistry and drug design.

  DOI：

  10.1111/cbdd.13918
• 作为产物：
  描述：

  在 盐酸 、 tin(ll) chloride 作用下， 以 水 为溶剂， 生成 (4-Amino-2-oxido-1,2,5-oxadiazol-2-ium-3-yl)-morpholin-4-ylmethanone
  参考文献：
  名称：

  通过胺的级联反应直接进入一氧化氮供体氮杂亚砜骨架。

  摘要：

  已开发出一种新颖的一锅级联方法，用于组装有价值的NO供体氮杂氮酮骨架。该构建策略涉及容易获得的胺的重氮化/偶氮偶合/消除/双重排级联序列。当前的方案使得能够生成多种阵列的氮杂氨醛酮，包括先前难以接近的杂芳基取代的氮杂氨醛酮（25个实例，产率为70-97％），并且在非常温和的条件下具有良好的官能团耐受性。初步的NO释放研究表明，氮杂syndones能够在很宽的浓度范围内产生NO。该方法为氮-氧杂环化合物的开发提供了一种新方法，在医学和材料科学领域具有潜在的应用前景。

  DOI：

  10.1002/chem.201903526