2,4-dimethoxy-6-(3',7'-dimethylocta-2'(E),6'-dienyl)phenol

• 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: 2,4-dimethoxy-6-(3',7'-dimethylocta-2'(E),6'-dienyl)phenol
• 英文别名: 6-geranyl-2,4-dimethoxyphenol；2-geranyl-4,6-dimethoxyphenol；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-4,6-dimethoxyphenol
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: BLPAGILLHJXPQH-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-6-(3',7'-dimethylocta-2'(E),6'-dienyl)phenol 在 sodium dithionite 、 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 2-geranyl-6-methoxy-1,4-hydroquinone
  参考文献：
  名称：

  Anti-inflammatory and Antimalarial Meroterpenoids from the New Zealand Ascidian Aplidium scabellum

  摘要：

  Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellones A (2) D (5). The benzo[c]chromene-7,10-dione scaffold contained within scabellones A D is particularly rare among natural products. The structures were elucidated by interpretation of NMR data. Scabellone B was also identified as a moderately potent, nontoxic inhibitor of Plasmodium falciparum.

  DOI：

  10.1021/jo201654h
• 作为产物：
  描述：

  重氮甲烷 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 2,4-dimethoxy-6-(3',7'-dimethylocta-2'(E),6'-dienyl)phenol
  参考文献：
  名称：

  Dermatotoxic phenolics from glandular trichomes of Phacelia campanularia and P. pedicellata

  摘要：

  DOI：

  10.1016/s0031-9422(00)81220-0

文献信息

• Catalytic Asymmetric Bromocyclization of Polyenes
  作者：Ramesh C. Samanta、Hisashi Yamamoto

  DOI：10.1021/jacs.6b13193

  日期：2017.2.1

  The first catalytic asymmetric bromonium ion-induced polyene cyclization has been achieved by using a chiral BINOL-derived thiophosphoramide catalyst and 1,3-dibromo-5,5-dimethylhydantoin as an electrophilic bromine source. Bromocyclization products are obtained in high yields, with good enantiomeric ratios and high diastereoselectivity, and are abundantly found as scaffolds in natural products.

  通过使用手性 BINOL 衍生的硫代磷酰胺催化剂和 1,3-二溴-5,5-二甲基乙内酰脲作为亲电溴源，实现了第一个催化不对称溴离子诱导的多烯环化。溴环化产物以高产率获得，具有良好的对映体比例和高非对映选择性，并且在天然产物中作为支架被大量发现。
• Evaluation of Cancer-Preventive Activity and Structure–Activity Relationships of 3-Demethylubiquinone Q2, Isolated from the Ascidian Aplidium glabrum, and its Synthetic Analogs
  作者：Sergey N. Fedorov、Oleg S. Radchenko、Larisa K. Shubina、Nadezhda N. Balaneva、Ann M. Bode、Valentin A. Stonik、Zigang Dong

  DOI：10.1007/s11095-005-8813-4

  日期：2006.1

  3-Demethylubiquinone Q2 (1) was isolated from the ascidian Aplidium glabrum. The cancer-preventive properties and the structure–activity relationship for 3-demethylubiquinone Q2 (1) and 12 of its synthetic analogs (3–14) are reported. Compounds 3–14, having one or several di- or triprenyl substitutions and quinone moieties with methoxyls in different positions, were synthesized. The cancer-preventive properties of compounds 1 and 3–14 were tested in JB6 Cl41 mouse skin cells, using a variety of assessments, including the methanethiosulfonate (MTS) assay, flow cytometry, and soft agar assay. Statistical nonparametric methods were used to confirm statistical significance. All quinones tested were shown to inhibit JB6 Cl41 cell transformation, to induce apoptosis, AP-1, and NF-κB activity, and to inhibit p53 activity. The most promising effects were indicated for compounds containing two isoprene units in a side chain and a methoxyl group at the para-position to a polyprenyl substitution. Quinones 1 and 3–14 demonstrated cancer-preventive activity in JB6 Cl41 cells, which may be attributed to the induction of p53-independent apoptosis. These activities depended on the length of side chains and on the positions of the methoxyl groups in the quinone part of the molecule.

  3-Demethylubiquinone Q2 (1)是从腹足动物 Aplidium glabrum 中分离出来的。报告了 3-去甲基泛醌 Q2 (1) 及其 12 种合成类似物（3-14）的防癌特性和结构-活性关系。化合物 3-14 具有一个或多个二烯丙基或三烯丙基取代，醌基在不同位置具有甲氧基。在 JB6 Cl41 小鼠皮肤细胞中测试了化合物 1 和 3-14 的防癌特性，采用了多种评估方法，包括甲硫代磺酸盐（MTS）测定法、流式细胞仪和软琼脂测定法。采用非参数统计方法确认统计意义。结果表明，所有测试的醌类化合物都能抑制 JB6 Cl41 细胞转化，诱导细胞凋亡、AP-1 和 NF-κB 活性，并抑制 p53 活性。侧链中含有两个异戊二烯单元、对位上含有一个甲氧基基团以取代多戊烯基的化合物的效果最为显著。醌 1 和 3-14 在 JB6 Cl41 细胞中显示出防癌活性，这可能是由于诱导了 p53 依赖性凋亡。这些活性取决于侧链的长度和醌分子中甲氧基的位置。
• [EN] THERAPEUTIC QUINONES<br/>[FR] QUINONES THERAPEUTIQUES
  申请人：UNIV MINNESOTA

  公开号：WO2006034392A2

  公开（公告）日：2006-03-30

  The present invention provides quinone and hydroquinone compounds that have, for example, anti-cancer activity.
• Anti-inflammatory and Antimalarial Meroterpenoids from the New Zealand Ascidian <i>Aplidium scabellum</i>
  作者：Susanna T. S. Chan、A. Norrie Pearce、Ana H. Januario、Michael J. Page、Marcel Kaiser、Rene J. McLaughlin、Jacquie L. Harper、Victoria L. Webb、David Barker、Brent R. Copp

  DOI：10.1021/jo201654h

  日期：2011.11.4

  Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellones A (2) D (5). The benzo[c]chromene-7,10-dione scaffold contained within scabellones A D is particularly rare among natural products. The structures were elucidated by interpretation of NMR data. Scabellone B was also identified as a moderately potent, nontoxic inhibitor of Plasmodium falciparum.
• Dermatotoxic phenolics from glandular trichomes of Phacelia campanularia and P. pedicellata
  作者：Gary W. Reynolds、Eloy Rodriguez

  DOI：10.1016/s0031-9422(00)81220-0

  日期：1986.1