3,5,4'-triacetoxy-bibenzyl | 89946-04-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,5,4'-triacetoxy-bibenzyl
• 英文别名: [4-[2-(3,5-Diacetyloxyphenyl)ethyl]phenyl] acetate；[4-[2-(3,5-diacetyloxyphenyl)ethyl]phenyl] acetate
• CAS: 89946-04-3
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: QRJHAIBGAUNYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白藜芦醇 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 12.0h， 生成 3,5,4'-triacetoxy-bibenzyl
  参考文献：
  名称：

  Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues

  摘要：

  The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4'-acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4'-triacetylresveratrol (3), 3,5,4'-tributanoylresveratrol (6), and 3, 4, 5'-trioctanoylresveratrol (9) afforded derivatives 4, 5, 7, 8, 10, and 11. Further resveratrol analogues (12-18) were obtained through methylation and hydrogenation reactions, whereas the 3,4,4'-trimethoxystilbene (19) was obtained by complete synthesis. Resveratrol and its lipophylic analogues were subjected to cell-growth inhibition bioassays towards DU-145 human prostate cancer cells. Compounds 2-19 showed cell-growth inhibition activity comparable to or higher than resveratrol (GI(50) = 24.09 muM), displaying low or very low toxicity against non-tumorigenic human fibroblast cells. Comparison of the trimethoxy stilbenes 12 (GI(50) = 2.92 muM) and 19 (GI(50) = 25.39 muM) indicates that the position of the substituents is important for the activity. The marked activity of methyl ethers 12, 13, and 18 in comparison with that of the corresponding esters suggests that the different chemical reactivity, rather than steric factors, strongly influences the activity.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.08.003

文献信息

• MOLECULARLY IMPRINTED POLYMERS
  申请人：Hearn Milton T. W.

  公开号：US20120052757A1

  公开（公告）日：2012-03-01

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

  本发明提供了设计分子印迹聚合物（MIPs）的方法，这些方法在从各种生物加工原料和废弃物中提取生物活性化合物方面具有应用。本发明进一步针对由本发明方法设计的MIPs。
• Identification of dihydrostilbenes in Pholidota chinensis as a new scaffold for GABAA receptor modulators
  作者：Diana C. Rueda、Angela Schöffmann、Maria De Mieri、Melanie Raith、Evelyn A. Jähne、Steffen Hering、Matthias Hamburger

  DOI：10.1016/j.bmc.2014.01.008

  日期：2014.2

  A dichloromethane extract of stems and roots of Pholidota chinensis (Orchidaceae) enhanced GABA-induced chloride currents (I-GABA) by 132.75 +/- 36.69% when tested at 100 mu g/mL in a two-micro-electrode voltage clamp assay, on Xenopus laevis oocytes expressing recombinant alpha(1)beta(2)gamma S-2 GABA(A) receptors. By means of an HPLC-based activity profiling approach, the three structurally related stilbenoids coelonin (1), batatasin III (2), and pholidotol D (3) were identified in the active fractions of the extract. Dihydrostilbene 2 enhanced I-GABA by 1512.19 +/- 176.47% at 300 mu M, with an EC50 of 52.51 +/- 16.96 mu M, while compounds 1 and 3 showed much lower activity. The relevance of conformational flexibility for receptor modulation by stilbenoids was confirmed with a series of 13 commercially available stilbenes and their corresponding semisynthetic dihydro derivatives. Dihydrostilbenes showed higher activity in the oocyte assay than their corresponding stilbenes. The dihydro derivatives of tetramethoxy-piceatannol (12) and pterostilbene (20) were the most active among these derivatives, but they showed lower efficiencies than compound 2. Batatasin III (2) showed high efficiency but no significant subunit specificity when tested on the receptor subtypes alpha(1)beta(2)gamma(2)s, alpha(2)beta(2)gamma(2)s, alpha(3)beta(2)gamma(2)s, alpha(4)beta(2)gamma(2)s, alpha(5)beta(2)gamma(2)s, alpha(1)beta(1)gamma(2)s, and alpha(1)beta(3)gamma(2)s. Dihydrostilbenes represent a new scaffold for GABAA receptor modulators. (C) 2014 Elsevier Ltd. All rights reserved.
• US9572815B2
  申请人：——

  公开号：US9572815B2

  公开（公告）日：2017-02-21
• [EN] MOLECULARLY IMPRINTED POLYMERS<br/>[FR] POLYMÈRES À EMPREINTES MOLÉCULAIRES
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2010085851A1

  公开（公告）日：2010-08-05

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
• Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues
  作者：Venera Cardile、Laura Lombardo、Carmela Spatafora、Corrado Tringali

  DOI：10.1016/j.bioorg.2004.08.003

  日期：2005.2

  The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4'-acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4'-triacetylresveratrol (3), 3,5,4'-tributanoylresveratrol (6), and 3, 4, 5'-trioctanoylresveratrol (9) afforded derivatives 4, 5, 7, 8, 10, and 11. Further resveratrol analogues (12-18) were obtained through methylation and hydrogenation reactions, whereas the 3,4,4'-trimethoxystilbene (19) was obtained by complete synthesis. Resveratrol and its lipophylic analogues were subjected to cell-growth inhibition bioassays towards DU-145 human prostate cancer cells. Compounds 2-19 showed cell-growth inhibition activity comparable to or higher than resveratrol (GI(50) = 24.09 muM), displaying low or very low toxicity against non-tumorigenic human fibroblast cells. Comparison of the trimethoxy stilbenes 12 (GI(50) = 2.92 muM) and 19 (GI(50) = 25.39 muM) indicates that the position of the substituents is important for the activity. The marked activity of methyl ethers 12, 13, and 18 in comparison with that of the corresponding esters suggests that the different chemical reactivity, rather than steric factors, strongly influences the activity.(C) 2004 Elsevier Inc. All rights reserved.