(E)-2-(3,7-dimethylocta-2,6-dienyl)-1,5-dimethoxy-3-methylbenzene | 83036-48-0

• 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: (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,5-dimethoxy-3-methylbenzene
• 英文别名: (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-1,5-dimethoxy-3-methylbenzene；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,5-dimethoxy-3-methylbenzene
• CAS: 83036-48-0
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: MGVICBUFGBBWCU-XNTDXEJSSA-N

物化性质

• 沸点：
  405.6±33.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,5-二羟基甲苯 在 三氟化硼乙醚 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成 (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,5-dimethoxy-3-methylbenzene
  参考文献：
  名称：

  Antiproliferative effect and apoptotic activity of linear geranylphenol derivatives from phloroglucinol and orcinol

  摘要：

  Sixteen synthetic linear derivatives geranylphenols, were obtained from phloroglucinol and orcinol, and cytotoxic activity was evaluated in vitro against cancer cell lines (HT-29, PC-3, MDA-MB231, DU-145) and one non-tumor cell line, human dermal fibroblast (HDF). IC50 values were determined at concentrations of 0-100 mu M of each compound for 72 h. Compounds 12, 13, 17, 21, 22 and 25, showed cytotoxic activity. To elucidate whether these compounds reduce cell viability by inducing apoptosis, cell lines MCF-7, PC-3 and DHF were treated with each active compound 12, 13, 17, 21, 22 and 25 and were examined after Hoechst 33342 staining. The compounds 12, 13 and 17 induced apoptosis in various cancer cell lines, as shown by nuclear condensation and/or fragmentation. In addition, it was found that compounds 12 and 13, induced changes in mitochondrial membrane permeability in those cancer cell lines. Such induction was associated with the depletion of mitochondrial membrane potential. These activities led to the cleavage of caspases inducing the cell death process. (C) 2016 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2016.01.016

文献信息

• Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities
  作者：Hitoshi Kamauchi、Takumi Oda、Kanayo Horiuchi、Koichi Takao、Yoshiaki Sugita

  DOI：10.1016/j.bmc.2019.115156

  日期：2020.1

  natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values < 25 μM) and the inhibition mode and molecular docking of two (8c and 16c) were investigated. Compounds inhibiting MAO-B activity were additionally tested for their ability to protect

  合成了27种天然产物状的聚异戊二烯基酚和醌，并使用人单胺氧化酶B（MAO-B）和SH-SY5Y细胞测试了它们的神经保护活性。八种化合物抑制了MAO-B（IC50值<25μM），并研究了两种化合物（8c和16c）的抑制模式和分子对接。还测试了抑制MAO-B活性的化合物保护SH-SY5Y细胞免于过氧化物损伤的能力。三种衍生物（3c，8c和16c）同时具有MAO-B抑制和神经保护作用。结构活性关系研究表明，酚羟基和较长的侧链对于这两种活性都很重要。
• AN EFFICIENT REGIO- AND STEREOSPECIFIC ALKENYLATION OF PHENOLIC ETHERS BY PRENYL AND GERANYL DIISOPROPYL PHOSPHATES
  作者：Shuki Araki、Shin-ichi Manabe、Yasuo Butsugan

  DOI：10.1246/cl.1982.797

  日期：1982.6.5

  Prenyl and geranyl diisopropyl phosphates readily alkenylate a variety of phenolic ethers regio- and stereospecifically without any appreciable side reactions.

  异戊二烯基和香叶基二异丙基磷酸酯很容易使各种酚醚区域和立体特异性地烯基化，而没有任何明显的副反应。