methyl 5-(3-hydroxypropyl)-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate | 108294-21-9

• 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 5-(3-hydroxypropyl)-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate
• CAS: 108294-21-9
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: JZUWAPWBDLWAFE-XMJAAHAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 5-(3-hydroxypropyl)-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以93%的产率得到methyl 5-(carboxyethyl)-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate
  参考文献：
  名称：

  Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid analogs

  摘要：

  A series of eicosatetraenes (2-24) were designed, synthesized, and evaluated in vitro for inhibitory activity against 5-lipoxygenase (20000g supernatant from homogenized rat basophilic leukemia cells). All compounds were found to be active with the potencies (IC50's) ranging from 0.19 to 97 microM. Compounds containing the hydroxamic acid functionality (10-12) exhibited the best activity (IC50 = 0.19-2.8 microM). The most potent inhibitor was 5-[(hydroxyamino)carbonyl]methyl]-6,8,11,14-eicosatetraenoic acid (11), which was 10 times more active than the C-1 hydroxamates of arachidonic acid or 5-HETE. Cyclization of the linear eicosanoids 2 and 14 in the C-1 to C-5 region produced compounds (21 and 24, respectively) with several-fold greater potency.

  DOI：

  10.1021/jm00390a010
• 作为产物：
  描述：

  1-bromo-2,5-undecadiyne 在 喹啉 、 Pd-BaSO₄ copper(l) iodide 、 乙基溴化镁 、 四丁基氟化铵 、 氢气 、 溴 、 1,2-双(二苯基膦)乙烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， -78.0~75.0 ℃ 、101.33 kPa 条件下， 反应 50.75h， 生成 methyl 5-(3-hydroxypropyl)-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate
  参考文献：
  名称：

  Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid analogs

  摘要：

  A series of eicosatetraenes (2-24) were designed, synthesized, and evaluated in vitro for inhibitory activity against 5-lipoxygenase (20000g supernatant from homogenized rat basophilic leukemia cells). All compounds were found to be active with the potencies (IC50's) ranging from 0.19 to 97 microM. Compounds containing the hydroxamic acid functionality (10-12) exhibited the best activity (IC50 = 0.19-2.8 microM). The most potent inhibitor was 5-[(hydroxyamino)carbonyl]methyl]-6,8,11,14-eicosatetraenoic acid (11), which was 10 times more active than the C-1 hydroxamates of arachidonic acid or 5-HETE. Cyclization of the linear eicosanoids 2 and 14 in the C-1 to C-5 region produced compounds (21 and 24, respectively) with several-fold greater potency.

  DOI：

  10.1021/jm00390a010