2,3,4,6-tetrakis(34,5-tribenzyloxybenzoyl)-D-glucose

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 2,3,4,6-tetrakis(34,5-tribenzyloxybenzoyl)-D-glucose
• 英文别名: 2,3,4,6-tetrakis(3,4,5-tris(benzyloxy)benzoyl)-D-glucopyranose；2,3,4,6-tetra-O-(3,4,5-tri-O-benzylgalloyl)-D-glucopyranose；[(2R,3R,4S,5R)-6-hydroxy-3,4,5-tris[[3,4,5-tris(phenylmethoxy)benzoyl]oxy]oxan-2-yl]methyl 3,4,5-tris(phenylmethoxy)benzoate
• 化学式: C₁₁₈H₁₀₀O₂₂
• 分子量: 1870.08
• InChiKey: CCZHHYVCHSXATB-APNBDJIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.4
• 重原子数：
  140
• 可旋转键数：
  49
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1,7-庚二酰氯 、 2,3,4,6-tetrakis(34,5-tribenzyloxybenzoyl)-D-glucose 在 palladium on activated charcoal 三乙胺 、 氢气 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 36.0h， 以60%的产率得到1,1'-O-2,2',3,3',4,4',6,6'-tetrakis(3,4,5-trihydroxybenzoyl)-D,D'-glucopyranosylpimelate
  参考文献：
  名称：

  In vitro and in vivo inhibition of LPS-induced tumor necrosis factor-α production by dimeric gallotannin analogues

  摘要：

  Designed dimeric gallotannin analogues featuring two tetragalloylglucopyranose cores connected by various hydrocarbon linkers inhibit tumor necrosis factor-alpha secretion from lipopolysaccharide-stimulated human peripheral blood mononuclear cells by up to 53% (5-24 muM concentration range) compared to control. Comparable suppression of tumor necrosis factor-alpha levels (similar to 50% vs control) was observed in the plasma of rats co-treated with lipopolysaccharide and specific tannin analogues selected for their lack of interleukin 1-beta stimulating activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00251-6
• 作为产物：
  描述：

  1-O-(o-nitrobenzyl)-2,3,4,6-tetra-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranose 在 水 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 以86%的产率得到2,3,4,6-tetrakis(34,5-tribenzyloxybenzoyl)-D-glucose
  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

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。
• Ellagitannin Chemistry. Syntheses of Tellimagrandin II and a Dehydrodigalloyl Ether-Containing Dimeric Gallotannin Analogue of Coriariin A
  作者：Ken S. Feldman、Kiran Sahasrabudhe

  DOI：10.1021/jo9816966

  日期：1999.1.1

  The first chemical synthesis of the naturally occurring ellagitannin tellimagrandin II is reported. Key steps of the synthesis include the atropselective oxidative coupling of suitably protected galloyl rings at the O(4) and O(6) positions of a glucopyranose core, and the stereoselective acylation of the derived anomeric alcohol with a galloyl chloride. In addition, the synthesis of a novel gallotannin-ellagitannin

  天然存在的鞣花单宁tellimagrandin II的首次化学合成已有报道。合成的关键步骤包括在吡喃葡萄糖核心的O（4）和O（6）位置适当保护的没食子酰基环的atropselective氧化偶联，和衍生的异头醇与没食子酰氯的立体选择性酰化。另外，描述了新的没食子鞣质-鞣花单宁杂交体的合成。该二聚体构建体依赖于杂Diels-Alder环加成/还原性重排序列，以从基于单体五烷基酰葡萄糖的邻醌递送完整骨架。
• [EN] GALLOTANNINS AND ELLAGITANNINS AS REGULATORS OF CYTOKINE RELEASE<br/>[FR] GALLOTANIN ET ELLAGITANIN EN TANT QUE REGULATEURS DE LA LIBERATION DE CYTOKINES
  申请人：PENN STATE RES FOUND

  公开号：WO2001036436A1

  公开（公告）日：2001-05-25

  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.

  本发明涉及使用没食子酸和榄香酸类物质增加或抑制细胞因子的分泌的方法和手段。首选的抑制细胞因子释放的化合物是二聚没食子酸，其具有使化合物的碳水化合物核心错位的连接分子。首选的促进细胞因子释放的没食子酸和榄香酸类包括一个二芳基醚连接单元。与结构更复杂的榄香酸类相比，本发明的化合物结构更简单，易于合成且更有效。
• GALLOTANNINS AND ELLIGITANNINS AS REGULATORS OF CYTOKINE RELEASE
  申请人：FELDMAN KENNETH S.

  公开号：US20080070850A1

  公开（公告）日：2008-03-20

  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.

  本发明描述了使用没食子酸单宁和榄皮酸单宁增加或抑制细胞因子分泌的方法和手段。优选的细胞因子释放抑制化合物是具有链接分子的二聚没食子酸单宁，该链接分子使化合物的碳水化合物核心错位。优选的细胞因子释放促进没食子酸单宁和榄皮酸单宁包括一个二芳基醚链接单元。与结构更为复杂的榄皮酸单宁相比，本发明的化合物结构更简单，更易于合成，且更具有活性。
• GALLOTANNINS AND ELLAGITANNINS AS REGULATORS OF CYTOKINE RELEASE
  申请人：THE PENN STATE RESEARCH FOUNDATION

  公开号：EP1232169A1

  公开（公告）日：2002-08-21