5-amino-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid | 108294-37-7

• 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: 5-amino-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid
• 英文别名: 5-Amino-icosa-6,8,11,14-tetraenoic acid；(6E,8Z,11Z,14Z)-5-aminoicosa-6,8,11,14-tetraenoic acid
• CAS: 108294-37-7
• 化学式: C₂₀H₃₃NO₂
• 分子量: 319.488
• InChiKey: VJQKFJDCPRJRMM-XTDASVJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 以86%的产率得到6-(1(E),3(Z),6(Z),9(Z)-pentadecatetraenyl)-2-piperidone
  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：

  methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate 在 lithium hydroxide 、 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 24.5h， 生成 5-amino-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid
  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

文献信息

• Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid analogs
  作者：Francis A. J. Kerdesky、Steven P. Schmidt、James H. Holms、Richard D. Dyer、George W. Carter、Dee W. Brooks

  DOI：10.1021/jm00390a010

  日期：1987.7

  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.