1,2,3,4,6-戊-O-(3,4,5-三-O-苄基没食子酰)-beta-D-吡喃葡萄糖 | 70424-95-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 1,2,3,4,6-戊-O-(3,4,5-三-O-苄基没食子酰)-beta-D-吡喃葡萄糖
• 英文名称: 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-β-D-glucopyranose
• 英文别名: β-D-glucopyranose-1,2,3,4,6-pentakis[3,4,5-tris(phenylmethoxy)benzoate]；1,2,3,4,6-penta-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranose；β-D-glucopyranose pentakis[3,4,5-tris(phenylmethoxy)benzoate]；1,2,3,4,6-pentakis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranose；β-D-Glucopyranose Pentakis[3,4,5-tris(phenylmethoxy)-benzoate]；Pentakis-O-(tri-O-benzyl-galloyl)-β-glucose；1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[[3,4,5-tris(phenylmethoxy)benzoyl]oxy]oxan-2-yl]methyl 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 70424-95-2；122625-60-9
• 化学式: C₁₄₆H₁₂₂O₂₆
• 分子量: 2292.56
• InChiKey: DXBOPZWOODFFKH-JKUAIIEZSA-N

物化性质

• 熔点：
  59-63°C
• 溶解度：
  可溶于氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  30
• 重原子数：
  172
• 可旋转键数：
  61
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  279
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-戊-O-(3,4,5-三-O-苄基没食子酰)-beta-D-吡喃葡萄糖 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到1,2,3,4,6-O-五没食子酰葡萄糖
  参考文献：
  名称：

  天然产物的高效全合成，以及不自然

  摘要：

  天然产物的合成短（8）， （10）和非天然（13）是基于所述苄没食子酸的高效酯化反应达到5与α，β-吡喃葡萄糖11和4分别。

  DOI：

  10.1016/s0040-4020(97)00702-3
• 作为产物：
  描述：

  a-无水葡萄糖酯 、 3,4,5-tris(benzyloxy)benzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,3,4,6-戊-O-(3,4,5-三-O-苄基没食子酰)-beta-D-吡喃葡萄糖
  参考文献：
  名称：

  Anomeric selectivity in the synthesis of galloyl esters of d-glucose

  摘要：

  The anomeric selectivity of the ester formation between D-glucopyranose and gallic acid was investigated under a variety of conditions. A new protocol was established that allows performing the reaction under conditions where mutarotation is very slow. Highly alpha- or beta-selective transformations are possible when starting with alpha- or beta-D-glucopyranose, respectively. Due to the kinetic anomeric effect, a high (x-selectivity is more difficult to achieve than a high beta-selectivity. The new methodology presented in this article was compared with established procedures for the synthesis of gallotannins. In addition to the advantages of a high yield and an easy purification protocol, the new procedure uniquely allowed for a highly selective synthesis of alpha-products. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.10.024

文献信息

• Gallotannins and ellagitannins as regulators of cytokine release
  申请人：The Penn State Research Foundation

  公开号：US07288273B1

  公开（公告）日：2007-10-30

  A means and method for increasing or inhibiting the secretion of cytokines using gallotannins and ellagitannins is described. The preferred cytokine release inhibiting compounds are dimeric gallotannins having a linker molecule that misaligns the carbohydrate cores of the compounds. The preferred cytokine release promoting gallotannins and ellagitannins include a diaryl ether linker unit. In comparison to the more structurally complex ellagitannins, the compounds of this invention are structurally simpler, easier to synthesize, and more potent.

  描述了一种使用没食子单宁和鞣花单宁增加或抑制细胞因子分泌的方法和手段。首选的细胞因子释放抑制化合物是具有连接分子的二聚没食子单宁，该连接分子使化合物的碳水化合物核心错位。首选的促进细胞因子释放的没食子单宁和鞣花单宁包括二芳基醚连接单元。与结构更复杂的鞣花单宁相比，本发明的化合物结构更简单、更容易合成且更有效。
• Gallotannins and Tannic Acid: First Chemical Syntheses and In Vitro Inhibitory Activity on Alzheimer’s Amyloid β-Peptide Aggregation
  作者：Tahiri Sylla、Laurent Pouységu、Grégory Da Costa、Denis Deffieux、Jean-Pierre Monti、Stéphane Quideau

  DOI：10.1002/anie.201411606

  日期：2015.7.6

  against Alzheimer’s disease has unveiled several plant polyphenols that are capable of inhibiting the formation of toxic β‐amyloid fibrils. Gallic acid based gallotannins are among these polyphenols, but their antifibrillogenic activity has thus far been examined using “tannic acid”, a commercial mixture of gallotannins and other galloylated glucopyranoses. The first total syntheses of two true gallotannins

  在寻找对抗阿尔茨海默氏病的新先导化合物的过程中，对天然产物的筛选揭示了几种能够抑制有毒β-淀粉样蛋白原纤维形成的植物多酚。在这些多酚中有基于没食子酸的没食子鞣质，但是迄今为止，已经使用“鞣酸”（一种鞣花酸和其他没食子酰化吡喃葡萄糖的商业混合物）检查了它们的抗原纤维形成活性。现在描述两种真实的没食子鞣质，六没食子酰基吡喃葡萄糖和十加铝基化的化合物的首次总合成，该化合物的结构通常用于描绘“鞣酸”。这些去甲没食子鞣质和更简单的没食子酸酯化的葡萄糖衍生物均在体外抑制淀粉样蛋白β肽（Aβ）的聚集，并且单没食子酸酯化的α-葡糖醇和天然β-六没糖基葡萄糖被证明是最强的抑制剂。
• 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。
• Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US09096501B2

  公开（公告）日：2015-08-04

  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.

  该发明涉及抑制纤溶酶原激活物-1（PAI-1）的化合物及其在治疗与升高的PAI-1相关的任何疾病或症状中的用途。该发明包括但不限于使用这些化合物来调节脂质代谢和治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• [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。