2-<(E)-3,7-dimethyl-2,6-octadienyl>-1,3-dimethoxy-5-methylbenzene | 83036-47-9

• 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: 2-<(E)-3,7-dimethyl-2,6-octadienyl>-1,3-dimethoxy-5-methylbenzene
• 英文别名: (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,3-dimethoxy-5-methylbenzene；(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-dimethoxy-5-methylbenzene；2,6-dimethoxy-1-geranyl-4-methylbenzene；(E)-2-(3,7-Dimethylocta-2,6-dien-1-yl)-1,3-dimethoxy-5-methylbenzene (10)；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3-dimethoxy-5-methylbenzene
• CAS: 83036-47-9
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: IZXKCEUPZYAGKC-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

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 2-<(E)-3,7-dimethyl-2,6-octadienyl>-1,3-dimethoxy-5-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

• 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。
• A General Approach for the Synthesis of Phenolic Natural Products. Facile Syntheses of Grifolin and Colletochlorins B and D
  作者：Hiroyuki Saimoto、Jiro Ueda、Hitoshi Sashiwa、Yoshihiro Shigemasa、Tamejiro Hiyama

  DOI：10.1246/bcsj.67.1178

  日期：1994.4

  is established for the synthesis of phenolic compounds having terpenoid side chains: (1) protection of the phenolic hydroxyls in the aromatic precursor by ether formation, (2) coupling the aromatic part with a terpenoid bromide, and (3) deprotection to regenerate the hydroxyl groups. This strategy was successfully applied to the synthesis of colletochlorins B and D and grifolin. Some of the colletochlorin

  为合成具有萜类侧链的酚类化合物建立了一般方法：(1) 通过醚形成保护芳族前体中的酚羟基，(2) 将芳族部分与萜类溴化物偶联，以及 (3) 脱保护以再生羟基。该策略已成功应用于炭疽菌素 B 和 D 以及灰树花素的合成。发现一些炭疽菌素衍生物可抑制 P388 的细胞生长。
• 2-Prenylated<i>m</i>-dimethoxybenzenes as potent inhibitors of 15-lipo-oxygenase: inhibitory mechanism and SAR studies
  作者：Atena Jabbari、Hamid Sadeghian、Alireza Salimi、Mina Mousavian、Seyed M. Seyedi、Mehdi Bakavoli

  DOI：10.1111/cbdd.12779

  日期：2016.9

  dimethoxybenzenes were synthesized and their inhibitory potency against soybean 15‐Lipo‐oxygenase (L1; EC 1,13,11,12) was determined. Among the synthetic compounds, 2,6‐dimethoxy‐1‐isopentenyl‐4‐methylbenzene, 2,6‐dimethoxy‐1‐geranyl‐4‐methylbenzene, and 2,6‐dimethoxy‐1‐farnesyl‐4‐methylbenzene showed the most potent inhibitory activity with IC50 values of 7.6, 5.3, and 0.52 μm, respectively. For some of the compounds

  15脂加氧酶是一种能够在动植物中进行不饱和脂肪酸过氧化的含铁蛋白之一。在哺乳动物中已经证明了酶在炎症，敏感性和某些癌症的形成中的关键作用。酶的重要性导致了机理研究，产物分析和抑制剂合成的发展。在这项研究中，合成了一系列烯丙基和异戊二烯基二甲氧基苯，并确定了它们对大豆15-脂氧合酶的抑制作用（L1； EC 1,13,11,12）。在合成化合物中，2,6-二甲氧基-1-异戊烯基-4-甲基苯，2,6-二甲氧基-1-香叶基-4-甲基苯和2,6-二甲氧基-1-法呢基-4-甲基苯显示最多。 IC 50值为7.6、5.3和0.52的 有效抑制活性μ米，分别。对于某些化合物，SAR研究表明其抑制能力和酶-配体相互作用之间的可接受关系。除SAR研究外，自由基清除评估结果还表明，电子性能是上述化合物抑制脂加氧酶效能的主要因素。根据理论研究表明，通过平面度固定，邻甲氧基氧与次甲基氢原子之间的CH…O分子内氢键是2
• Antiproliferative effect and apoptotic activity of linear geranylphenol derivatives from phloroglucinol and orcinol
  作者：Lautaro Taborga、Luis Espinoza、Alejandra Moller、Héctor Carrasco、Mauricio Cuellar、Joan Villena

  DOI：10.1016/j.cbi.2016.01.016

  日期：2016.3

  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.