methyl (6E,8Z,11Z)-5-thia-6,8,11-eicosatrienoate | 125197-85-5

• 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 (6E,8Z,11Z)-5-thia-6,8,11-eicosatrienoate
• 英文别名: 4-Pentadeca-1,3,6-trienylsulfanyl-butyric acid methyl ester；methyl 4-[(1E,3Z,6Z)-pentadeca-1,3,6-trienyl]sulfanylbutanoate
• CAS: 125197-85-5
• 化学式: C₂₀H₃₄O₂S
• 分子量: 338.555
• InChiKey: BCCIWBSBPMCVDG-CVWBSBFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (6E,8Z,11Z)-5-thia-6,8,11-eicosatrienoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以97%的产率得到(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：

  dodec-3-yn-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 29.07h， 生成 methyl (6E,8Z,11Z)-5-thia-6,8,11-eicosatrienoate
  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;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：——
• Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes
  作者：Rudolf Hanko、Michael D. Hammond、Romanis Fruchtmann、Joerg Pfitzner、Graham A. Place

  DOI：10.1021/jm00166a013

  日期：1990.4

  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.