2-methyl-2-(isosorbide-5-nitrate-2-)1,3-benzodioxin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2-methyl-2-(isosorbide-5-nitrate-2-)1,3-benzodioxin-4-one
• 英文别名: ismna；[(3S,3aR,6R,6aS)-3-[(2-methyl-4-oxo-1,3-benzodioxin-2-yl)oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate
• 化学式: C₁₅H₁₅NO₉
• 分子量: 353.285
• InChiKey: CLBHSMAYWJDRQD-SUMILCEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-单硝酸异山梨酯 、 邻乙酰水杨酰氯 以 氯仿 为溶剂， 反应 1.0h， 以58%的产率得到2-methyl-2-(isosorbide-5-nitrate-2-)1,3-benzodioxin-4-one
  参考文献：
  名称：

  Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin

  摘要：

  Two isomeric aspirin derivatives of isosorbide-5-mononitrate (ISMN) were prepared and evaluated as potential mutual prodrugs of aspirin and nitric oxide. The hydrolysis of both compounds was studied in pH 7.4 phosphate buffer solution, buffered alpha -chymotrypsin solution and 10% buffered rabbit plasma. The benzodioxin-4-one derivative was hydrolysed to salicylic acid and ISMN acetate in buffer solution (t(1/2) 32. t h), 10% buffered rabbit plasma (t(1/2) 25.7 min) and alpha -chymotrypsin (t(1/2) 86.6 min). The carboxylic acid ester derivative ISMNA was hydrolysed via the salicylate ester in buffer solution (t(1/2) 48.5 h) but was rapidly and almost exclusively hydrolysed to aspirin and ISMN in plasma solution (t(1/2) 2.8 min). The hydrolysis appeared to be enzyme mediated as it was suppressed by co-incubation with eserine. ISMNA was evaluated for its ability to inhibit platelet aggregation in rabbit PRP in response to the following agonists: arachidonic acid (AA) (100 muM), ADP (1.2 muM) phorbol ester (0.5 muM). platelet activating factor (PAF) (5 nM) and the thromboxane mimic U46619 (1.5 muM). ISMNA suppressed platelet response to AA at 1 muM whereas 10 muM aspirin showed no inhibitory effects. (C) 2001 Published by Elsevier Science B.V.

  DOI：

  10.1016/s0928-0987(01)00183-x