(1E)-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethanimidate | 501093-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E)-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethanimidate
• CAS: 501093-76-1
• 化学式: C₁₃H₂₀N₄O₉
• 分子量: 376.323
• InChiKey: FCYNMQHCRCKEEQ-URYVQPGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  5-氨基-3-(4-吗啉基)-1,2,3-恶二唑盐酸盐 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (1E)-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethanimidate
  参考文献：
  名称：

  New Glycosidase Activated Nitric Oxide Donors:  Glycose and 3-Morphorlinosydnonimine Conjugates

  摘要：

  To achieve site specific delivery of nitric oxide (NO), a new class of glycosidase activated NO donors has been developed. Glucose, galactose, and N-acetylneuraminic acid were covalently coupled to 3-morphorlinosydnonimine (SIN-1), a mesoionic heterocyclic NO donor, via a carbamate linkage at the anomeric position. The beta-glycosides were successfully prepared for these conjugates, while the alpha-glycosidic compounds were very unstable. The new stable sugar-NO conjugates could release NO in the presence of glycosidases. Such NO prodrugs may be used as enzyme activated NO donors in biomedical research.

  DOI：

  10.1021/jo050010o