(6E,8Z,11Z,14Z)-5-(hydroxymethyl)-6,8,11,14-eicosatetraenoic acid | 83606-25-1

• 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: (6E,8Z,11Z,14Z)-5-(hydroxymethyl)-6,8,11,14-eicosatetraenoic acid
• 英文别名: 5-Hydroxymethyl-icosa-6,8,11,14-tetraenoic acid；(6E,8Z,11Z,14Z)-5-(hydroxymethyl)icosa-6,8,11,14-tetraenoic acid
• CAS: 83606-25-1
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: FLETVOYHEXEYPG-XTDASVJISA-N

物化性质

• 沸点：
  496.6±33.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴-2辛炔 在 喹啉 、 Pd-BaSO₄ lithium hydroxide 、 copper(l) iodide 、 乙基溴化镁 、 氢气 、 溴 、 三氯化铁 、 1,2-双(二苯基膦)乙烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 异丙醇 、 乙腈 为溶剂， -78.0~75.0 ℃ 、101.33 kPa 条件下， 反应 86.0h， 生成 (6E,8Z,11Z,14Z)-5-(hydroxymethyl)-6,8,11,14-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 activities of eicosanoid compounds
  作者：Yoshinobu Arai、Katsuichi Shimoji、Mitoshi Konno、Yoshitaka Konishi、Shigehiro Okuyama、Sadahiko Iguchi、Masaki Hayashi、Tsumoru Miyamoto、Masaaki Toda

  DOI：10.1021/jm00355a015

  日期：1983.1

  Ten eicosanoid compounds (3, 6, 9, 11, 12, 15, 18, 21, 23, and 25), methyl (6E,8Z,11Z,14Z)-5-hydroxy-6,8,11,14-eicosatetraenoate (5-HETE, 10), leukotriene A4 (26), and (5S,6E,8E,10E,12RS,14E)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid (5,12-diHETE, 27) were prepared and their inhibitory activities against the 5-lipoxygenase from guinea pig polymorphonuclear leukocytes (PMNL) were tested. 5,6-Methanoleukotriene

  十种类花生酸化合物（3、6、9、11、12、15、18、21、23和25），甲基（6E，8Z，11Z，14Z）-5-羟基-6,8,11,14-二十碳四烯酸酯（5-HETE，10），白三烯A4（26）和（5S，6E，8E，10E，12RS，14E）-5,12-二羟基-6,8,10,14-二十碳四烯酸（5,12-制备diHETE（27），并测试其对豚鼠多形核白细胞（PMNL）对5-脂氧合酶的抑制活性。5,6-甲醇二烯三烯A4（18）特别是5-脂氧合酶的有效和特异性抑制剂，而不会抑制环氧合酶和12-脂氧合酶。白三烯A4、5-HETE和5,12-diHETE在微摩尔浓度下也具有对5-脂氧合酶的抑制活性，可调节细胞内过敏反应的慢反应性物质的形成。
• Synthesis of (.+-.)-carba-analogs of 5-HPETE and leukotriene A4,unstable intermediates of slow-reacting substance (SRS).
  作者：Yoshinobu Arai、Mitoshi Konno、Katsuichi Shimoji、Yoshitaka Konishi、Haruki Niwa、Masaaki Toda、Masaki Hayashi

  DOI：10.1248/cpb.30.379

  日期：——

  The carba-analogs of 5-HPETE and leukotriene A4, unstable intermediates of slow-reacting substance (SRS), were synthesized. These carbaanalogs inhibited the 5-lipoxygenase. The carba-analog of leukotriene A4 was a particularly potent specific inhibitor of the 5-lipoxygenase.

  5-HPETE和白三烯A4的碳-类似物是慢反应物质（SRS）的不稳定中间体，它们被合成出来。这些碳-类似物抑制了5-脂氧合酶。白三烯A4的碳-类似物是5-脂氧合酶的一种特别有效的特异性抑制剂。
• 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.