(-)-8,8'-epi-aristoligone | 97116-36-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (-)-8,8'-epi-aristoligone
• 英文别名: 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 97116-36-4
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: UCHGPGXURWMCBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-8,8'-epi-aristoligone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以100%的产率得到Opt.-inakt. 4-Hydroxy-6.7-dimethoxy-2.3-dimethyl-1-(3.4-dimethoxy-phenyl)-1.2.3.4-tetrahydro-naphthalin
  参考文献：
  名称：

  Aryltetralols from Holostylis reniformis and syntheses of lignan analogous

  摘要：

  Two new lignans, an aryltetralol and its methyl ether analogous, were isolated from Holostylis reniformis (Aristolochiaceae) together with futokadsurin C and (-)-8'-epi-aristoligone. The latter was also obtained as an enantiomeric mixture by synthesis and was transformed into aryltetralols and aryltetralenes that were subjected to chiral-HPLC separations. The compound structures were determined by spectroscopic methods. Several of these lignans had their antiplasmodial activity (against Plasmodium falciparum, W2 clone, anti-HRPII) and toxicity to mammalian kidney cells (MDL50) evaluated. (-)-Cyclogalgravin and (-)-aristoligol exhibited activity (IC50 similar to 10.8 and 8.4 mu M, respectively), the latter exhibited lower toxicity. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2015.06.001
• 作为产物：
  描述：

  (E)-1,2-二甲氧基-4-(1-丙烯基)苯 生成 (-)-8,8'-epi-aristoligone
  参考文献：
  名称：

  TAKEHTANI, TEHTSUYA;KOTANI, EHJITI;TOBINAGA, SEHJSE

  摘要：

  DOI：

文献信息

• Stereocontrolled Syntheses of Tetralone- and Naphthyl-Type Lignans by a One-Pot Oxidative [3,3] Rearrangement/Friedel-Crafts Arylation
  作者：Jordan C. T. Reddel、Kelly E. Lutz、Abdallah B. Diagne、Regan J. Thomson

  DOI：10.1002/anie.201307659

  日期：2014.1.27

  The development of a stereoselective one‐pot oxidative [3,3] sigmatropic rearrangement/Friedel–Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone‐ and naphthyl‐type lignan natural products, many of which display anti‐malarial activity.

  据报道，立体选择性单锅氧化[3,3]σ重排/ Friedel-Crafts芳基化反应可提供对映体富集的苯甲基化合物。几种四氢萘酮和萘基木脂素天然产物的简明合成证明了这种新转化的效用，其中许多具有抗疟疾活性。
• Aryltetralols from Holostylis reniformis and syntheses of lignan analogous
  作者：Marcos D.P. Pereira、Matheus R. Ferreira、Gisele B. Messiano、Isabela Penna Cerávolo、Lucia M.X. Lopes、Antoniana U. Krettli

  DOI：10.1016/j.phytol.2015.06.001

  日期：2015.9

  Two new lignans, an aryltetralol and its methyl ether analogous, were isolated from Holostylis reniformis (Aristolochiaceae) together with futokadsurin C and (-)-8'-epi-aristoligone. The latter was also obtained as an enantiomeric mixture by synthesis and was transformed into aryltetralols and aryltetralenes that were subjected to chiral-HPLC separations. The compound structures were determined by spectroscopic methods. Several of these lignans had their antiplasmodial activity (against Plasmodium falciparum, W2 clone, anti-HRPII) and toxicity to mammalian kidney cells (MDL50) evaluated. (-)-Cyclogalgravin and (-)-aristoligol exhibited activity (IC50 similar to 10.8 and 8.4 mu M, respectively), the latter exhibited lower toxicity. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• TAKEHTANI, TEHTSUYA;KOTANI, EHJITI;TOBINAGA, SEHJSE
  作者：TAKEHTANI, TEHTSUYA、KOTANI, EHJITI、TOBINAGA, SEHJSE

  DOI：——

  日期：——