2,3',4,5'-tetramethoxybibenzyl | 24131-34-8

• 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: 2,3',4,5'-tetramethoxybibenzyl
• 英文别名: 2,4,3',5'-tetramethoxy-bibenzyl；1-[2-(3,5-Dimethoxyphenyl)ethyl]-2,4-dimethoxybenzene；1-[2-(2,4-dimethoxyphenyl)ethyl]-3,5-dimethoxybenzene
• CAS: 24131-34-8
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: DCXIHQRTYWSKKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3',4,5'-tetramethoxybibenzyl 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 2,4,3',5'-Tetramethoxy-5,2'-dibrom-diphenylethan
  参考文献：
  名称：

  从 2,4,3', 5'-四羟基-二苯基乙烷合成双香豆素基乙烷衍生物。关于双香豆素乙烷和双香豆素乙烷的第一次通讯

  摘要：

  2,4,3', 5'-四羟基-二苯基乙烷（2a）可以用乙酰乙酸酯/硫酸转化成双香豆素乙烷衍生物，由于其化学性质和光谱，被归类为1-[4-甲基- 7-羟基-香豆素基-(6)]-2-4-甲基-5-羟基-香豆素基-(7)-乙烷(1a)。实验从 2,4,3', 5'-四羟基芪 (1a) 或通过 1,2-二溴-1-[2,4-二乙酰氧基苯基]-2-[3,5-二乙酰氧基苯基]-乙烷 (11) 双香豆素基乙烯衍生物3不成功。

  DOI：

  10.1002/ardp.19703031209
• 作为产物：
  描述：

  2,4,3',5'-tetramethoxy-deoxybenzoin 在 盐酸 、 amalgamated zinc 作用下， 生成 2,3',4,5'-tetramethoxybibenzyl
  参考文献：
  名称：

  Mongolsuk et al., Journal of the Chemical Society, 1957, p. 2231

  摘要：

  DOI：

文献信息

• Computational Analysis and Biological Activities of Oxyresveratrol Analogues, the Putative Cyclooxygenase-2 Inhibitors
  作者：Nathjanan Jongkon、Boonwiset Seaho、Ngampuk Tayana、Saisuree Prateeptongkum、Nongnaphat Duangdee、Panichakorn Jaiyong

  DOI：10.3390/molecules27072346

  日期：——

  Polyphenols are a large family of naturally occurring phytochemicals. Herein, oxyresveratrol was isolated from ethanolic crude extracts of Artocarpus lacucha Buch.-Ham., and chemically modified to derive its lipophilic analogues. Biological screening assays showed their inhibitory potency against cyclooxygenase-2 (COX-2) with very low cytotoxicity to the MRC-5 normal cell lines. At the catalytic site of COX-2, docking protocols with ChemPLP, GoldScore and AutoDock scoring functions were carried out to reveal hydrogen bonding interactions with key polar contacts and hydrophobic pi-interactions. For more accurate binding energetics, COX-2/ligand complexes at the binding region were computed in vacuo and implicit aqueous solvation using M06-2X density functional with 6-31G+(d,p) basis set. Our computational results confirmed that dihydrooxyresveratrol (4) is the putative inhibitor of human COX-2 with the highest inhibitory activity (IC50 of 11.50 ± 1.54 µM) among studied non-fluorinated analogues for further lead optimization. Selective substitution of fluorine provides a stronger binding affinity; however, lowering the cytotoxicity of a fluorinated analogue to a normal cell is challenging. The consensus among biological activities, ChemPLP docking score and the binding energies computed at the quantum mechanical level is obviously helpful for identification of oxyresveratrol analogues as a putative anti-inflammatory agent.

  多酚是一大类天然存在的植物化学物质。在此，从艾塔果（Artocarpus lacucha Buch.-Ham.）的乙醇粗提物中分离出了氧化白藜芦醇，并进行了化学修饰以得到其亲脂类似物。生物筛选实验显示它们对环氧合酶-2（COX-2）具有抑制作用，对MRC-5正常细胞系的细胞毒性非常低。在COX-2的催化位点上，使用ChemPLP、GoldScore和AutoDock评分函数进行对接协议，以揭示与关键极性接触和疏水π相互作用的氢键作用。为了获得更准确的结合能，使用M06-2X密度泛函和6-31G+(d,p)基组，在真空和隐式水溶剂中计算了COX-2/配体复合物在结合区域的结合能。我们的计算结果确认，二氢氧化白藜芦醇（4）是人类COX-2的潜在抑制剂，其抑制活性最高（IC50为11.50±1.54微摩尔），在进一步的前导化合物优化研究中是非氟化类似物中最佳的。选择性地取代氟可以提供更强的结合亲和力；然而，降低氟化类似物对正常细胞的细胞毒性是具有挑战性的。生物活性、ChemPLP对接评分和在量子力学水平计算的结合能之间的一致性显然有助于确定氧化白藜芦醇类似物作为潜在的抗炎剂。
• Process for extraction and separation of oxyresveratrol from Artocarpus lakoocha Roxb
  申请人：Council of Scientific & Industrial Research

  公开号：US10376840B2

  公开（公告）日：2019-08-13

  The present invention relates to a process for separation of oxyresveratrol molecule from the extracted solution of Artocarpus lakoocha Roxb. through membrane application. The product can be obtained in excellent yield upto 81% in case of extraction using water as solvent and can be separated from the extracted mixture upto 98% using indigenously developed nanofiltration membrane. Only the desired Trans isomer is obtained and no cis isomerization takes place during the extraction process.

  本发明涉及一种通过膜应用从拉古查树（Artocarpus lakoocha Roxb.）提取液中分离氧白藜芦醇分子的工艺。在用水作为溶剂萃取的情况下，可以获得高达 81% 的极高产率，使用自主研发的纳滤膜，可以从萃取混合物中分离出高达 98% 的产品。在萃取过程中，只能获得所需的反式异构体，而不会发生顺式异构化。
• Dang, Y.; Geise, H. J., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 5, p. 375 - 380
  作者：Dang, Y.、Geise, H. J.

  DOI：——

  日期：——
• Chemical transformations of oxyresveratrol (trans-2,4,3′,5′-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent
  作者：Kittisak Likhitwitayawuid、Acom Sornsute、Boonchoo Sritularak、Poonsakdi Ploypradith

  DOI：10.1016/j.bmcl.2006.08.018

  日期：2006.11

  From oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene 1), seven derivatives were prepared, including trans-2-methoxy-4,3',5'-trihydroxystilbene (2), trans-2,3'-dimethoxy-4,5'-dihydroxystilbene (3), trans-4,3'-dimethoxy-2,5'-dihydroxystilbene (4), trans-2,4,3',5'-tetramethoxystilbene (5) and cis-2,4,3',5'-tetramethoxystilbene (6), 2,4,3',5'-tetrahydroxybibenzyl (7), and 2,4,3',5'-tetramethoxybibenzyl (8). The tetrahydroxybibenzyl 7, a hydrogenation product of 1, exhibited more potent tyrosinase inhibitory activity than the parent compound, without cytotoxicity. A kinetic study revealed that 7 was a reversible and non-competitive inhibitor of mushroom tyrosinase with L-dopa as the substrate. Analysis of the K-i values indicated that 7 has a slightly higher affinity to the enzyme than 1. Compound 6, a tetra-O-methylated analogue of 1 with cis-configuration, was deprived of inhibitory effect on the enzyme tyrosinase, but showed very strong cytotoxicity against the human cancer cells KB, BC, and NCI-H187, with potency comparable to those of the anticancer agents ellipticine and doxorubicin. Data on the tyrosinase inhibitory activity and cytotoxicity of 1-8 indicated that O methylation on stilbene 1 destroyed anti-tyrosinase activity but generated cytotoxicity. Thus, facile preparations of a potent tyrosinase inhibitor (7) and a strong cytotoxic agent (6) from the natural product 1 were achieved through simple chemical reactions. (c) 2006 Elsevier Ltd. All rights reserved.
• Takaoka, 1940, vol. <III> 3, p. 1,15
  作者：Takaoka

  DOI：——

  日期：——