1,2,3,4,6-pentakis[O-(3,4,5-tribenzyloxybenzoyl)]-D-glucopyranoside

• 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-tribenzyloxybenzoyl)]-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R)-3,4,5,6-tetrakis[[3,4,5-tris(phenylmethoxy)benzoyl]oxy]oxan-2-yl]methyl 3,4,5-tris(phenylmethoxy)benzoate
• 化学式: C₁₄₆H₁₂₂O₂₆
• 分子量: 2292.56
• InChiKey: DXBOPZWOODFFKH-XGKIMOHUSA-N

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-pentakis[O-(3,4,5-tribenzyloxybenzoyl)]-D-glucopyranoside 在 1% Pd/C 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以99%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：

  Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos

  摘要：

  By use of the model virus, expressing the HCV envelope proteins E1 and E2, bioassay guided separation of the MeOH extract from Rosa rugosa Thunb. disclosed tellimagrandin I (1) together with eugeniin (2) and casuarictin (3) as the potent HCV invasion inhibitors. Furthermore, structure-activity relationship analysis of some relative tannins including the synthesized analogs elucidated the partial structures crucial for potent activity of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.084
• 作为产物：
  描述：

  D-葡萄糖 、 3,4,5-三苄氧基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,3,4,6-pentakis[O-(3,4,5-tribenzyloxybenzoyl)]-D-glucopyranoside
  参考文献：
  名称：

  1,2,3,4,6-五[[O-（3,4,5-三羟基苯甲酰基）]-α，β-D-吡喃葡萄糖（PGG）类似物：设计，合成，抗肿瘤和抗氧化活性

  摘要：

  1,2,3,4,6-五[[O-（（3,4,5-三羟基苯甲酰基）]-α，β-D-吡喃葡萄糖（PGG）12的抗氧化活性已有报道，其中游离的OH基团在PGG中似乎对活动至关重要。为了探索基于PGG的化合物作为化学治疗剂并分析PGG中特定OH基团对抗癌活性的贡献，我们设计并合成了27种PGG苯甲酸和肉桂酸类似物。测试了这些类似物对两种人肺（A549和H1299）和两种人结肠（HCT116和HT29）癌细胞系的细胞毒性。化合物12（PGG）对HCT116和A549细胞具有最高的细胞毒性，IC50分别为1.61 µM和3.02 µM。相反，化合物16（1,2,3,4,6-戊基[-O-（4-羟基-3-甲氧基苯甲酰基）]-α，β-D-吡喃葡萄糖，PVG）最有效地杀死HT29和H1299细胞，IC50分别为1.76 µM和3.65 µM，表明间甲氧基和对羟基对观察到的细胞毒性具有相互影响。而且，肉桂酸类似物

  DOI：

  10.1016/j.carres.2016.04.021

文献信息

• Designing Allosteric Inhibitors of Factor XIa. Lessons from the Interactions of Sulfated Pentagalloylglucopyranosides
  作者：Rami A. Al-Horani、Umesh R. Desai

  DOI：10.1021/jm500311e

  日期：2014.6.12

  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.
• METHODS AND COMPOSITIONS FOR TREATING DIABETES MELLITIS
  申请人：Ohio University

  公开号：EP1545554A1

  公开（公告）日：2005-06-29
• EP1545554A4
  申请人：——

  公开号：EP1545554A4

  公开（公告）日：2006-06-14
• Methods and compositions for treating diabetes mellitis
  申请人：Chen Xiaozhuo

  公开号：US20060058243A1

  公开（公告）日：2006-03-16

  Methods for modulating diabetes, impaired glucose tolerance, gestational diabetes and glucose resistance in a mammal, particularly a human. In one embodiment the method comprises administering a gallotannin composition to a mammal in need of the same. The gallotannin composition comprises one or more select hydrolysable gallotannins. In another embodiment the method comprises administering a gallotannin variant composition comprising one ore more select gallotannin variant compounds to the subject. Methods of preventing or treating weight gain in a subject. The method comprises administering the gallotannin composition of the present invention, the gallotannin variant composition of the present invention, or a combination of the gallotannin composition of the present invention and the gallotannin variant composition of the present invention to the subject. The present invention also relates a gallotannin variant compound or a salt thereof, and a pharmaceutical composition comprising such compound or the salt thereof.
• [EN] METHODS AND COMPOSITIONS FOR TREATING DIABETES MELLITIS<br/>[FR] METHODES ET COMPOSITIONS PERMETTANT DE TRAITER LES DIABETES SUCRES
  申请人：UNIV OHIO

  公开号：WO2004009094A1

  公开（公告）日：2004-01-29

  Methods for modulating diabetes, impaired glucose tolerance, gestational diabetes and glucose resistance in a mammal, particularly a human. In one embodiment the method comprises administering a gallotannin composition to a mammal in need of the same. The gallotannin composition comprises one or more select hydrolysable gallotannins. In another embodiment the method comprises administering a gallotannin variant composition comprising one ore more select gallotannin variant compounds to the subject. Methods of preventing or treating weight gain in a subject. The method comprises administering the gallotannin composition of the present invention, the gallotannin variant composition of the present invention, or a combination of the gallotannin composition of the present invention and the gallotannin variant composition of the present invention to the subject. The present invention also relates a gallotannin variant compound or a salt thereof, and a pharmaceutical composition comprising such compound or the salt thereof.