4-[(4E,8E)-11-(3-furanyl)-4,8-dimethyl-4,8-undecadienyl]-2(5H)-furanone | 76343-80-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-[(4E,8E)-11-(3-furanyl)-4,8-dimethyl-4,8-undecadienyl]-2(5H)-furanone
• 英文别名: furospongolide；3-[(4E,8E)-11-(furan-3-yl)-4,8-dimethylundeca-4,8-dienyl]-2H-furan-5-one
• CAS: 76343-80-1
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: WCHKEOQZUQGPSS-ZTRBTYSCSA-N

物化性质

• 沸点：
  491.594±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.036±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(4E,8E)-11-(3-furanyl)-4,8-dimethyl-4,8-undecadienyl]-2(5H)-furanone 在 sodium hydroxide 、 水 作用下， 反应 24.0h， 生成
  参考文献：
  名称：

  Molecular-Targeted Antitumor Agents. 19. Furospongolide from a Marine Lendenfeldia sp. Sponge Inhibits Hypoxia-Inducible Factor-1 Activation in Breast Tumor Cells

  摘要：

  A natural product chemistry-based approach was employed to discover small-molecule inhibitors of the important tumor-selective molecular target hypoxia-inducible factor-1 (HIF-1). Bioassay-guided isolation of an active lipid extract of a Saipan collection of the marine sponge Lendenfeldia sp. afforded the terpene-derived furanolipid furospongolide as the primary inhibitor of hypoxia-induced HIF-1 activation (IC50 2.9 mu M, T47D breast tumor cells). The active component of the extract also contained one new cytotoxic scalarane sesterterpene and two previously reported scalaranes. Furospongolide blocked the induction of the downstream HIF-1 target secreted vascular endothelial growth factor (VEGF) and was shown to suppress HIF-1 activation by inhibiting the hypoxic induction of HIF-1 alpha protein. Mechanistic studies indicate that furospongolide inhibits HIF-1 activity primarily by suppressing tumor cell respiration via the blockade of NADH-ubiquinone oxidoreductase (complex I)-mediated mitochondrial electron transfer.

  DOI：

  10.1021/np800342s
• 作为产物：
  描述：

  8-hydroxygeranyl acetate 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 dilithium tetrachlorocuprate 、 5% Pd-BaSO4 、 氢气 、 copper(l) cyanide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 40.75h， 生成 4-[(4E,8E)-11-(3-furanyl)-4,8-dimethyl-4,8-undecadienyl]-2(5H)-furanone
  参考文献：
  名称：

  Synthesis of the Hypoxic Signaling Inhibitor Furospongolide

  摘要：

  以乙酸香叶酯为原料，通过八个线性步骤首次合成了海洋 HIF-1 抑制剂 furospongolide。关键步骤包括 Schlosser sp³-sp³ 交叉偶联和 δ-bromobutenolide 的 Sonogashira 烷炔化。

  DOI：

  10.1055/s-0030-1260329

文献信息

• Synthesis of the Hypoxic Signaling Inhibitor Furospongolide
  作者：John Boukouvalas、Vincent Albert

  DOI：10.1055/s-0030-1260329

  日期：2011.10

  The first synthesis of the marine HIF-1 inhibitor furospongolide has been achieved in eight linear steps from geranyl acetate. Key steps include Schlosser sp³-sp³ cross-coupling and Sonogashira alkynylation of β-bromobutenolide.

  以乙酸香叶酯为原料，通过八个线性步骤首次合成了海洋 HIF-1 抑制剂 furospongolide。关键步骤包括 Schlosser sp³-sp³ 交叉偶联和 δ-bromobutenolide 的 Sonogashira 烷炔化。
• Molecular-Targeted Antitumor Agents. 19. Furospongolide from a Marine <i>Lendenfeldia</i> sp. Sponge Inhibits Hypoxia-Inducible Factor-1 Activation in Breast Tumor Cells
  作者：Yang Liu、Rui Liu、Shui-Chun Mao、J. Brian Morgan、Mika B. Jekabsons、Yu-Dong Zhou、Dale G. Nagle

  DOI：10.1021/np800342s

  日期：2008.12.1

  A natural product chemistry-based approach was employed to discover small-molecule inhibitors of the important tumor-selective molecular target hypoxia-inducible factor-1 (HIF-1). Bioassay-guided isolation of an active lipid extract of a Saipan collection of the marine sponge Lendenfeldia sp. afforded the terpene-derived furanolipid furospongolide as the primary inhibitor of hypoxia-induced HIF-1 activation (IC50 2.9 mu M, T47D breast tumor cells). The active component of the extract also contained one new cytotoxic scalarane sesterterpene and two previously reported scalaranes. Furospongolide blocked the induction of the downstream HIF-1 target secreted vascular endothelial growth factor (VEGF) and was shown to suppress HIF-1 activation by inhibiting the hypoxic induction of HIF-1 alpha protein. Mechanistic studies indicate that furospongolide inhibits HIF-1 activity primarily by suppressing tumor cell respiration via the blockade of NADH-ubiquinone oxidoreductase (complex I)-mediated mitochondrial electron transfer.