[(3S,3aR,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-[(1S)-1-[2-(4-methylpiperazin-1-yl)acetyl]oxypentyl]benzoate | 1428866-55-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(3S,3aR,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-[(1S)-1-[2-(4-methylpiperazin-1-yl)acetyl]oxypentyl]benzoate
• CAS: 1428866-55-0
• 化学式: C₂₅H₃₅N₃O₉
• 分子量: 521.568
• InChiKey: KDEBVZFYMJWIMC-BRUFLCKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-丁基-1(3H)-异苯并呋喃酮 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， -20.0~50.0 ℃ 、310.27 kPa 条件下， 反应 29.67h， 生成 [(3S,3aR,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 2-[(1S)-1-[2-(4-methylpiperazin-1-yl)acetyl]oxypentyl]benzoate
  参考文献：
  名称：

  Novel Hybrids of Optically Active Ring-Opened 3-n-Butylphthalide Derivative and Isosorbide as Potential Anti-Ischemic Stroke Agents

  摘要：

  In search of novel anti-ischemic stroke agents with higher potency than a known drug 3-n-butylphthalide (NBP), a series of hybrids ((S)- and (R)-5a-f) from optically active ring-opened NBP derivative and isosorbide were synthesized for evaluating their anti-ischemic stroke activity. Compound (S)-5e displayed the strongest activity in inhibiting the adenosine diphosphate (ADP) and arachidonic acid (AA)-induced platelet aggregation in vitro, with 10.0- and 8.4-fold more effectiveness than (S)-NBP, respectively. Furthermore, (S)-5e was stable in artificial gastrointestinal fluids and could penetrate the blood-brain barrier (BBB) with an appreciate lipid/water partition coefficient relative to (S)-NBP. More importantly, oral treatment with (S)-5e protected from acute thrombosis and inhibited the ischemia/reperfusion-related brain injury in animals. Our findings suggest that (S)-5e may be promising for further evaluation for the intervention of ischemic stroke.

  DOI：

  10.1021/jm4001693