D-吡喃葡萄糖 1,2,3,4,6-五(3,4,5-三羟基苯甲酸酯) | 50678-27-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: D-吡喃葡萄糖 1,2,3,4,6-五(3,4,5-三羟基苯甲酸酯)
• 中文别名: D-吡喃葡萄糖1,2,3,4,6-五(3,4,5-三羟基苯甲酸酯)；3-[4-(苄氧基)苯基]丙酸
• 英文名称: pentagalloyl glucose
• 英文别名: 1,2,3,4,6-pentagalloylglucose；D-Glucopyranose, pentakis(3,4,5-trihydroxybenzoate)；[(2R,3R,4S,5R)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 50678-27-8
• 化学式: C₄₁H₃₂O₂₆
• 分子量: 940.689
• InChiKey: QJYNZEYHSMRWBK-PPPHSYQWSA-N

物化性质

• 熔点：
  160 °C (decomp)
• 沸点：
  1365.7±65.0 °C(Predicted)
• 密度：
  2.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  67
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  444
• 氢给体数：
  15
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  D-吡喃葡萄糖 1,2,3,4,6-五(3,4,5-三羟基苯甲酸酯) 以 丙酮 为溶剂， 反应 480.0h， 生成 1,2,3,4,6-O-五没食子酰葡萄糖
  参考文献：
  名称：

  [EN] PGG SEPARATION AND PURIFICATION
  [FR] SEPARATION ET PURIFICATION DE PGG

  摘要：

  一种简单、廉价且高效的方法，用于分离和纯化α-和β-形式的五-O-没食子醛-D-葡萄糖（PGG），无需高效液相色谱。本文提供的方法可用于从含有α-PGG和β-PGG以及其他化学品的混合物中分离α-PGG或β-PGG。从含有50%或更多α-PGG和50%或更少β-PGG的样品中分离α-PGG的方法包括以下步骤：向样品中加入水以溶解PGG；搅拌PGG和水使PGG溶解；过滤出任何未溶解的颗粒；并让过滤后的溶液静置直到结晶形成。

  公开号：

  WO2005070943A1
• 作为产物：
  描述：

  1,2,3,4,6-pentakis[O-(3,4,5-tribenzyloxybenzoyl)]-D-glucopyranoside 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 10.0h， 生成 D-吡喃葡萄糖 1,2,3,4,6-五(3,4,5-三羟基苯甲酸酯)
  参考文献：
  名称：

  Designing Allosteric Inhibitors of Factor XIa. Lessons from the Interactions of Sulfated Pentagalloylglucopyranosides

  摘要：

  We recently introduced sulfated pentagalloylglucopyranoside (SPGG) as an allosteric inhibitor of factor XIa (FXIa) (Al-Horani et al., J. Med Chem. 2013, 56, 867-878). To better understand the SPGG-FXIa interaction, we utilized eight SPGG variants and a range of biochemical techniques. The results reveal that SPGG's sulfation level moderately affected FXIa inhibition potency and selectivity over thrombin and factor Xa. Variation in the anomeric configuration did not affect potency. Interestingly, zymogen factor XI bound SPGG with high affinity, suggesting its possible use as an antidote. Acrylamide quenching experiments suggested that SPGG induced significant conformational changes in the active site of FXIa. Inhibition studies in the presence of heparin showed marginal competition with highly sulfated SPGG variants but robust competition with less sulfated variants. Resolution of energetic contributions revealed that nonionic forces contribute nearly 87% of binding energy suggesting a strong possibility of specific interaction. Overall, the results indicate that SPGG may recognize more than one anion-binding, allosteric site on FXIa. An SPGG molecule containing approximately 10 sulfate groups on positions 2 through 6 of the pentagalloylglucopyranosyl scaffold may be the optimal FXIa inhibitor for further preclinical studies.

  DOI：

  10.1021/jm500311e

文献信息

• Complete¹H and¹³C NMR assignments of a series of pergalloylated tannins
  作者：Serge Lavoie、Michael Ouellet、Pierre-Yves Fleury、Charles Gauthier、Jean Legault、André Pichette

  DOI：10.1002/mrc.4328

  日期：2016.2

  activities. Because these analogs were only partially characterized by NMR, we would like to report herein the complete H and C assignments of pergalloylated D-glucose (1), D-mannose (2), Dgalactose (3), D-xylose (4), L-ribose (5), L-arabinose (6), L-rhamnose (7), and D-fucose (8) by using a combination of one-dimensional and two-dimensional NMR experiments.

  单宁是广泛分布于植物界的次生代谢物。单宁的一个共同特征是它们的酚单元，它们可以连接在一起形成高度多样化的化学结构。由于这些化合物构成了摄入的食品和饮料的重要组成部分，因此对它们的生物效应进行了彻底的研究。最近，我们对加拿大山茱萸进行了植物化学研究，这是一种在北美野生生长的丰富开花植物，果实可食用。进行了初步的生物活性筛选，结果显示加拿大 C. 的提取物对 1 型单纯疱疹病毒具有活性。在生物测定引导的分级分离之后，鉴定了可水解的单宁。这些化合物之一，即 1,2,3,4,6-penta-O-galloyl-β-D-吡喃葡萄糖 (PGG)，已成为张最近审查的几项药物研究的主题。PGG 的生物学和药用特性多种多样，包括抗癌、抗氧化、抗诱变、抗炎、抗过敏、降胆固醇、抗凝、抗肾结石、抗惊厥、抗病毒和抗菌活性。此外，合成了一系列 PGG 类似物，发现它是刺激脂肪细胞葡萄糖转运的最佳支架。其中一些化合物也
• Plasminogen Activator Inhibitor-1 Inhibitors And Methods Of Use Thereof To Modulate Lipid Metabolism
  申请人：Lawrence Daniel A.

  公开号：US20090011055A1

  公开（公告）日：2009-01-08

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  该发明涉及纤溶酶原激活物-1（PAI-1）抑制剂化合物及其在治疗与升高的PAI-1相关的任何疾病或状况中的应用。该发明包括但不限于利用这些化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的疾病。
• [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。
• METHOD AND SYSTEM FOR EFFECTING CHANGES IN PIGMENTED TISSUE
  申请人：Moazed Kambiz Thomas

  公开号：US20110280909A1

  公开（公告）日：2011-11-17

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are nanoparticle compositions for lightening the pigmented tissues or treating a pigmented tissue related disease.

  描述了一种快速和可持续改变虹膜基质黑色素含量的黑色素细胞的方法和系统，从而改变眼睛的颜色。还描述了用于淡化有色组织或治疗有色组织相关疾病的纳米颗粒组合物。
• PHARMACEUTICAL COMPOSITIONS CONTAINING POLY(ADP-RIBOSE) GLYCOHYDROLASE INHIBITORS AND METHODS OF USING THE SAME
  申请人：——

  公开号：US20030078212A1

  公开（公告）日：2003-04-24

  The present invention relates to pharmaceutical compositions containing poly(ADP-ribose) glucohydrolase inhibitors, also known as PARG inhibitors, and methods of using the same for inhibiting or decreasing free radical induced cellular energy depletion, cell damage, or cell death. More particularly, the present invention relates to pharmaceutical compositions containing poly (ADP-ribose) glucohydrolase inhibitors such as glucose derivatives; lignin glycosides; hydrolysable tannins including gallotannins and ellagitannins; adenoside derivatives; acridine derivatives including 6,9-diamino-2-ethoxyacridine lactate monohydrate; tilorone analogs including tilorone R10.556, daunomycin or daunorubicin hydrochloride; ellipticine; proflavine; and other PARG inhibitors; and their method of use in treating or preventing diseases or conditions due to free radical induced cellular energy depletion and/or tissue damage resulting from cell damage or death due to necrosis, apoptosis, or combinations thereof.

  本发明涉及药物组合物，其包含聚(ADP-核糖)葡萄糖水解酶抑制剂，也称为PARG抑制剂，以及使用它们抑制或减少自由基引起的细胞能量耗竭、细胞损伤或细胞死亡的方法。更具体地说，本发明涉及药物组合物，其中包含聚(ADP-核糖)葡萄糖水解酶抑制剂，例如葡萄糖衍生物；木质素糖苷；可水解单宁，包括没食子酸单宁和榄皮酸单宁；腺苷衍生物；吖啶衍生物，包括6,9-二氨基-2-乙氧基吖啶乳酸单水合物；tilorone类似物，包括tilorone R10.556，多柔比星或多柔比星盐酸盐；椭圆酸；丙氟维明；以及其他PARG抑制剂；以及它们在治疗或预防由自由基引起的细胞能量耗竭和/或由细胞损伤或死亡引起的组织损伤的疾病或状况中的使用方法，包括坏死、凋亡或两者的组合。