2,3,4,6-tetra-O-galloyl-glucose | 93059-81-5

• 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-tetra-O-galloyl-glucose
• 英文别名: tetra-O-galloyl glucopyranose；2,3,4,6-tetragalloyl glucose；2,3,4,6-tetra-O-galloyl-D-glucose；2,3,4,6-Tetrakis-O-Galloyl-D-Glucopyranose；galloyl(-2)[galloyl(-3)][galloyl(-4)][galloyl(-6)]Glc；[(2R,3R,4S,5R)-6-hydroxy-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 93059-81-5
• 化学式: C₃₄H₂₈O₂₂
• 分子量: 788.583
• InChiKey: RJINLRBSXMOGAQ-KMNHUKDVSA-N

物化性质

• 沸点：
  1240.8±65.0 °C(Predicted)
• 密度：
  2.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  377
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  在 钯 氢气 作用下， 生成 2,3,4,6-tetra-O-galloyl-glucose
  参考文献：
  名称：

  On the basis for regioselective oxidation within a tetragalloylpyranose substrate

  摘要：

  Lead (N)-mediated oxidation of a benzyl 2,3,4,6-tetragalloylglucopyranoside leads only to coupling at the O(4)/O(6) galloyls, Competitive oxidation experiments with a series of positionally distinct phenolic galloyl analogs furnishes evidence that this unexpected regioselectivity stems from preferential oxidation at the O(6) galloyl ring. Companion studies with electronically dissimilar analogs provide support for a through-space component to O(6) galloyl oxidation selectivity in addition to steric and inductive influences. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01986-8

文献信息

• Ellagitannin Chemistry. The First Total Chemical Synthesis of an Ellagitannin Natural Product, Tellimagrandin I
  作者：Ken S. Feldman、Susan M. Ensel、Robert D. Minard

  DOI：10.1021/ja00084a015

  日期：1994.3

  Tellimagrandin I was synthesized by two different biogenetically patterned routes. One route featured diastereoselective galloyl ester coupling between the O(4) and O(6) galloyl moieties in a glucose-derived substrate bearing additional protected galloyl groups on 0(2) and 0(3). The second route relied on a completely diastereoslective and regioselective Pb(OAc) 4 -based oxidative coupling exclusively

  Tellimagrandin I 是通过两种不同的生物遗传学模式合成的。一种路线的特色是在葡萄糖衍生底物中的 O(4) 和 O(6) 没食子酰部分之间的非对映选择性没食子酰酯耦合，在 0(2) 和 0(3) 上具有额外的受保护没食子酰基团。第二种途径依赖于完全非对映选择性和区域选择性的基于 Pb(OAc) 4 的氧化偶联，仅在葡萄糖衍生底物中的 O(4) 和 O(6) 没食子酰酯之间进行氧化偶联，该底物具有 O(2)- O(6)。基于分子力学的构象分析为观察到的选择性提供了依据
• 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。
• Erectile Dysfunction Treatment
  申请人：——

  公开号：US20040247698A1

  公开（公告）日：2004-12-09

  A method for extracting compositions from a natural product, their pharmaceutical compositions, the pharmaceutical compounds, and their therapeutic uses as a sexual performance enhancer, in the treatment of erectile dysfunction, and in the treatment of hypertension in humans and animals.

  一种从天然产物中提取化合物的方法，以及它们的制药组合物、制药化合物，以及它们作为性能增强剂的治疗用途，用于治疗人类和动物的勃起功能障碍和高血压。
• YOSHIDA, TAKASHI;CHOU, TONG;NITTA, AYA;MIYAMOTO, KEN-ICHI;KOSHIURA, RYOZO+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1211-1217
  作者：YOSHIDA, TAKASHI、CHOU, TONG、NITTA, AYA、MIYAMOTO, KEN-ICHI、KOSHIURA, RYOZO+

  DOI：——

  日期：——
• JPH04275223A
  申请人：——

  公开号：JPH04275223A

  公开（公告）日：1992-09-30