1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-β-D-glucopyranose | 18482-96-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-β-D-glucopyranose
• 英文别名: Pentakis-(3,4,5-trimethoxybenzoyl)-beta-D-Glucose；[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trimethoxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trimethoxybenzoate
• CAS: 18482-96-7
• 化学式: C₅₆H₆₂O₂₆
• 分子量: 1151.09
• InChiKey: WQNLIZGZVLXBKJ-ZKGWKYPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  82
• 可旋转键数：
  31
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  279
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  甲醇 、 1,2,3,4,6-O-五没食子酰葡萄糖 在 acetate buffer 作用下， 以 水 为溶剂， 生成 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-β-D-glucopyranose
  参考文献：
  名称：

  Structure of gallotannins in Paeoniae Radix.

  摘要：

  从芍药根中均匀分离出鞣酸（多鞣酸葡萄糖），并通过13C核磁共振谱对其结构进行了阐明。

  DOI：

  10.1248/cpb.28.2850

文献信息

• [EN] GP120 -BINDING BENZENE COMPOUNDS AND SACCHARIDE COMPOUNDS<br/>[FR] COMPOSÉS DE BENZÈNES ET DE SACCHARIDES SE LIANT À GP120
  申请人：UNIV LEUVEN KATH

  公开号：WO2011085454A1

  公开（公告）日：2011-07-21

  The present invention provides for novel benzene compounds and saccharide compounds and for the use of said compounds for binding, titration (quantification), removing, purifying or separating the glycoprotein gp120, gp120 comprising viruses or cells infected with gp120 comprising viruses. The invention also provides for a method for the detection, binding, titration (quantification), removal, purification or separation of (or directing therapeutic or other agents to) gp120, gp120 comprising viruses or cells infected with gp120 comprising viruses. The invention further provides for the use of the compounds and for methods using the compounds for directing anti -viral drugs or other agents to gp120 comprising viruses or to gp120 comprising virus - infected cells. The present invention also provides processes for the preparation of said novel compounds.

  本发明提供了新型苯化合物和糖化合物，并用于结合、滴定（定量）、去除、纯化或分离含有糖蛋白gp120的化合物的用途，该gp120包括病毒或感染有包含gp120病毒的细胞。本发明还提供了一种用于检测、结合、滴定（定量）、去除、纯化或分离（或将治疗或其他药物引导至）gp120的方法，该gp120包括病毒或感染有包含gp120病毒的细胞。本发明进一步提供了利用这些化合物的用途，以及用于将抗病毒药物或其他药物引导至含有gp120的病毒或含有gp120病毒感染细胞的方法。本发明还提供了用于制备这些新型化合物的工艺。
• Improved anomeric selectivity for the aroylation of sugars
  作者：M. Teresa Barros、Christopher D. Maycock、Paula Rodrigues、Christine Thomassigny

  DOI：10.1016/j.carres.2004.02.015

  日期：2004.5

  bulky TMEDA as a base, good yields and improved anomeric selectivities were obtained for the aroylation of D-glucose over similar esterifications using pyridine. The reaction has been extended to mannose and the beta-anomer of pergalloylated mannose was predominantly obtained in one step by direct aroylation of the parent sugar.

  通过处理溶剂并使用庞大的TMEDA作为碱，与使用吡啶进行的类似酯化反应相比，D-葡萄糖的芳基化反应具有良好的收率和改进的端基选择性。该反应已扩展至甘露糖，主要通过亲代糖的直接芳基化在一个步骤中主要获得过泛酰化的甘露糖的β-端基异构体。
• Effects of Tannins from <i>Geum </i><i>j</i><i>aponicum </i>on the Catalytic Activity of Thrombin and Factor Xa of Blood Coagulation Cascade
  作者：Hui Dong、Shao-Xing Chen、R. Manjunatha Kini、Hong-Xi Xu

  DOI：10.1021/np9801458

  日期：1998.11.1

  Bioassay-guided fractionation of the MeOH extract of the whole plant of Geum japonicum led to the isolation of seven known tannins. They were identified by spectroscopic methods as penta-O-galloyl-beta-di-glucoside (1), pedunculagin (2), 2,3-(S)-hexahydroxydiphenoyl-D-glucose (3), tellimagrandin II (4), 2,6-di-O-galloyl-D-glucose (5), casuariin (6), and 5-desgalloylstachyurin (7). Compounds 1, 2, 4, 6, and 7 showed potent anticoagulant activity by significantly prolonging the clotting of rabbit plasma. The inhibitory effect of 2 was competitively directed against thrombin. Its IC50 values for inhibition of the enzymatic activity of thrombin on synthetic substrate and fibrinogen were 0.18 and 0.15 mu M, respectively. On the other hand, compounds 1, 4, 6, and 7 are mixed noncompetitive inhibitors of thrombin. Their IC50 values for inhibition of fibrinogen hydrolysis were twofold to sevenfold lower than those for the inhibition of synthetic substrate hydrolysis. Factor Xa was competitively inhibited by compounds 1, 2, 4, 6, and 7. The phenolic hydroxyl groups of the active tannins appear to play an important role in their inhibitory effect on the enzymes.
• Anomeric selectivity and influenza A virus inhibition study on methoxylated analogues of Pentagalloylglucose
  作者：Shaikh Qurat-ul-ain、Wei Wang、Meiting Yang、Na Du、Shengbiao Wan、Lijuan Zhang、Tao Jiang

  DOI：10.1016/j.carres.2014.10.011

  日期：2015.1

  Anomeric selectivity in galloylation of D-glucose and D-mannose with carboxylic acid was explored under steglich conditions. Base catalyst 4-dimethylaminopyridine favored the formation of alpha-anomers, while adding an acid and carbodiimide favored the formation of beta-anomers. Steric hindrance between alpha, beta-unsaturated acid and C-2 OH stereochemistry (adjacent carbon to anomeric) influenced anomeric selectivity for both D-glucose and D-mannose. The influenza A virus inhibition activities of the synthesized compounds were evaluated in Madin-Darby canine kidney cell line using the cytopathic effect inhibition assay. All the synthetic methoxylated analogues showed more considerable activity against influenza A virus than their corresponding acids, which indicated the sugar core as key functionality for anti-viral activity. The activities of trimethoxy-cinnamic acid Pentagalloylglucose analogues, 3 alpha, 3 beta, 4 alpha, and 4 beta (IC50, 109.1 mu M, 134.4 mu M, 119.5 mu M, 111.1 mu M, respectively) were better than those of trimethoxy- benzoic acid Pentagalloylglucose analogues, 1-alpha beta and 2 alpha, 2 beta (IC50, 209.8 mu M, 132.9 mu M, 161.2 mu M, respectively), which suggested that the double bond in cinnamic acid Pentagalloylglucose analogues makes the major contribution for influenza A virus inhibitory activity. Notably, several anomeric mixtures showed better activities than pure alpha or beta anomer and were almost two times more effective than Ribavirin, a clinically used anti-viral drug. (C) 2014 Elsevier Ltd. All rights reserved.
• NONAKA, GEN-ICHIRO;ISHIMATSU, MAKOTO;TANAKA, TAKASHI;NISHIOKA, ITSUO;NISH+, CHEM. AND PHARM. BULL., 35,(1987) N 8, 3127-3131
  作者：NONAKA, GEN-ICHIRO、ISHIMATSU, MAKOTO、TANAKA, TAKASHI、NISHIOKA, ITSUO、NISH+

  DOI：——

  日期：——