1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2,5,8-triyne | 98582-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2,5,8-triyne
• 英文别名: 2--tetrahydropyran；2-Tetradeca-2,5,8-triynoxyoxane
• CAS: 98582-21-9
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: GDDISTOIDIEZMY-UHFFFAOYSA-N

物化性质

• 沸点：
  430.7±45.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2,5,8-triyne 在 喹啉 、 Pd-BaSO₄ 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 38.75h， 生成 methyl 5-(2-hydroxyethyl)-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-溴-2辛炔 在 copper(l) iodide 、 乙基溴化镁 、 溴 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2,5,8-triyne
  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

• Eicosatetraenehydroxamates: inhibitors of 5-lipoxygenase
  作者：F.A.J. Kerdesky、J.H. Holms、S.P. Schmidt、R.O. Dyer、G.W. Carter

  DOI：10.1016/s0040-4039(00)98946-9

  日期：1985.1
• GUZMAN, ANGEL;MUCHOWSKI, JOSEPH M.
  作者：GUZMAN, ANGEL、MUCHOWSKI, JOSEPH M.

  DOI：——

  日期：——
• US4670465A
  申请人：——

  公开号：US4670465A

  公开（公告）日：1987-06-02
• 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.