methyl (2E)-8-oxo-5-thia-6-octenoate | 125197-78-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2E)-8-oxo-5-thia-6-octenoate
• 英文别名: methyl 4-[(E)-3-oxoprop-1-enyl]sulfanylbutanoate
• CAS: 125197-78-6
• 化学式: C₈H₁₂O₃S
• 分子量: 188.247
• InChiKey: DAVREXXRZZMQCL-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E)-8-oxo-5-thia-6-octenoate 在 lithium hydroxide 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 6.57h， 生成 (6E,8Z,11Z)-5-thia-6,8,11-eicosatrienoic acid
  参考文献：
  名称：

  Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes

  摘要：

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.

  DOI：

  10.1021/jm00166a013
• 作为产物：
  描述：

  丙炔醛 、 阿哌沙班杂质61 在 碘 、 sodium acetate 作用下， 生成 methyl (2E)-8-oxo-5-thia-6-octenoate
  参考文献：
  名称：

  Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes

  摘要：

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.

  DOI：

  10.1021/jm00166a013

文献信息

• HANKO, RUDOLF;PFITZNER, JOERG;HAMMOND, MICHAEL;PLACE, GRAHAM
  作者：HANKO, RUDOLF、PFITZNER, JOERG、HAMMOND, MICHAEL、PLACE, GRAHAM

  DOI：——

  日期：——
• HANKO, RUDOLF;HAMMOND, MICHAEL D.;FRUCHTMANN, ROMANIS;PFITZNER, JOERG;PLA+, J. MED. CHEM., 33,(1990) N, C. 1163-1170
  作者：HANKO, RUDOLF、HAMMOND, MICHAEL D.、FRUCHTMANN, ROMANIS、PFITZNER, JOERG、PLA+

  DOI：——

  日期：——