(11Z,13E)-eicosa-11,13-dienoic acid | 105835-45-8

• 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: (11Z,13E)-eicosa-11,13-dienoic acid
• 英文别名: (11Z,13E)-11,13-Eicosadienoic acid；(11Z,13E)-icosa-11,13-dienoic acid
• CAS: 105835-45-8
• 化学式: C₂₀H₃₆O₂
• 分子量: 308.505
• InChiKey: UNFHLCKMPAPDAZ-GOJKSUSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (11Z,13E)-eicosa-11,13-dienoic acid 以95%的产率得到
  参考文献：
  名称：

  HAVIV F.; RATAJCZYK J. D.; DENET R. W.; MARTIN Y. C.; DYER R. D.; CARTER +, J. MED. CHEM., 30,(1987) N 2, 254-263

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-1-碘-1-辛烯 在 copper(l) iodide 、 四(三苯基膦)钯 、 nickel boride 、 氢气 作用下， 以 二乙胺 为溶剂， 反应 3.0h， 生成 (11Z,13E)-eicosa-11,13-dienoic acid
  参考文献：
  名称：

  Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogs

  摘要：

  The structural requirements for inhibition of RBL-1 (rat basophilic leukemia) 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15-HETE, 1) were studied by systematic chemical modifications of the molecule at the hydroxyl and carboxyl groups, the double bonds, and the carboxylate and omega side chains. The most potent inhibitors were analogues that contained a 5,8-cis,cis-diene system and acted as alternate substrates for the enzyme. However, several analogues in which the 5,8-diene had been reduced were also found to inhibit the enzyme. Inhibition of 5-lipoxygenase by 15-hydroxyeicosa-11,13-dienoic acid (15-HEDE) analogues was optimal in compounds that generally contained a free carboxyl group, a carboxylate side chain of nine carbons, an omega side chain of five or six carbons, a cis,trans- or trans,cis-11,13-diene or 11,13-diyne system, and a 15-hydroxyl group. Conversion of 15-HEDE to its 16-membered lactone reduced but did not eliminate 5-lipoxygenase inhibitory activity. In contrast, a 3- to 10-fold enhancement of activity occurred when 5,15-diHETE (58) or 5-HETE (56) were cyclized to their respective delta-lactones. Molecular modeling of 15-HEDE analogues, modified in the C11-C15 region, showed that inactive analogues protrude into regions in space not occupied by active analogues. These structural studies indicate that multiple regions are important for 5-lipoxygenase inhibition by both 15-HETE and 15-HEDE analogues and that no single region plays a predominant role in inhibition.

  DOI：

  10.1021/jm00385a005

文献信息

• Suppression of carcinoma using high purity conjugated fatty acid
  申请人：——

  公开号：US20010018453A1

  公开（公告）日：2001-08-30

  Treatment of carcinoma in a human is disclosed, including administering a therapeutically effective amount of a fatty acid having four carbons with two conjugated double bonds formed by reacting an ester of a fatty acid with a tosyl chloride or a mesyl chloride, the fatty acid having four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogens, and a double bond is positioned between carbon three and four. The tosylate or mesylate of the ester of the fatty acid having the chain of four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogens, and a double bond is positioned between carbon three and four is reacted with diazabicyclo-undecene. The method includes administering to a human a highly purified fatty acid in accordance with the present invention.

  本发明公开了治疗人类癌症的方法，包括施用治疗有效量的脂肪酸，该脂肪酸具有四个碳原子，通过脂肪酸酯与甲苯磺酰氯或甲磺酰氯反应形成两个共轭双键，该脂肪酸具有四个碳原子，其中碳一含有一个氢和一个羟基，碳二含有两个氢，双键位于碳三和碳四之间。具有四个碳原子链的脂肪酸酯的对甲苯磺酸盐或甲磺酸盐与重氮双环十一烯反应，其中碳一含有一个氢和一个羟基，碳二含有两个氢，双键位于碳三和碳四之间。该方法包括向人类施用符合本发明的高纯度脂肪酸。
• HAVIV F.; RATAJCZYK J. D.; DENET R. W.; MARTIN Y. C.; DYER R. D.; CARTER +, J. MED. CHEM., 30,(1987) N 2, 254-263
  作者：HAVIV F.、 RATAJCZYK J. D.、 DENET R. W.、 MARTIN Y. C.、 DYER R. D.、 CARTER +

  DOI：——

  日期：——
• US6160141A
  申请人：——

  公开号：US6160141A

  公开（公告）日：2000-12-12
• US6342619B2
  申请人：——

  公开号：US6342619B2

  公开（公告）日：2002-01-29
• US6602908B2
  申请人：——

  公开号：US6602908B2

  公开（公告）日：2003-08-05