1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose | 111234-34-5

• 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)]-α-D-glucopyranose
• 英文别名: Pentakis-(3,4,5-trimethoxybenzoyl)-alpha-D-Glucose；[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis[(3,4,5-trimethoxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trimethoxybenzoate
• CAS: 111234-34-5
• 化学式: C₅₆H₆₂O₂₆
• 分子量: 1151.09
• InChiKey: WQNLIZGZVLXBKJ-WRZIUSKJSA-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：

  nupharin A 在 水 、 氢气 作用下， 生成 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose
  参考文献：
  名称：

  Novel hydrolyzable tannins from Nuphar Japonicum DC.

  摘要：

  从日本睡莲（Nuphar japonicum DC.，属于睡莲科）中分离出了两种没食子的鞣酸（I和II）和一种被称为nupharin A的榄仁鞣酸（III）。根据化学和光谱证据，I、II和III的结构分别被鉴定为1, 2, 6-三-O-没食子酸基-α-D-葡萄糖、1, 2, 3, 4, 6-五-O-没食子酸基-α-D-葡萄糖和1, 2, 6-三-O-没食子酸基-3, 4-(S)-六羟基二苯甲酮-α-D-葡萄糖。

  DOI：

  10.1248/cpb.30.1094

文献信息

• 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。
• 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。
• 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：——
• EP1171130A4
  申请人：——

  公开号：EP1171130A4

  公开（公告）日：2004-05-19