1,2,3,4,6-Penta-O-(3,4,5-Trimethoxybenzoyl)-D-Glucopyranose | 98543-10-3

• 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-Penta-O-(3,4,5-Trimethoxybenzoyl)-D-Glucopyranose
• 英文别名: [(2R,3R,4S,5R)-3,4,5,6-tetrakis[(3,4,5-trimethoxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trimethoxybenzoate
• CAS: 98543-10-3
• 化学式: C₅₆H₆₂O₂₆
• 分子量: 1151.09
• InChiKey: WQNLIZGZVLXBKJ-RXXNVMESSA-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：

  D-葡萄糖 、 3,4,5-三甲氧基苯甲酸 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-Penta-O-(3,4,5-Trimethoxybenzoyl)-D-Glucopyranose
  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

• 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。
• EP1171130A4
  申请人：——

  公开号：EP1171130A4

  公开（公告）日：2004-05-19
• [EN] PHARMACEUTICAL COMPOSITIONS CONTAINING POLY(ADP-RIBOSE) GLYCOHYDROLASE INHIBITORS AND METHODS OF USING THE SAME<br/>[FR] COMPOSITIONS PHARMACEUTIQUES CONTENANT DES INHIBITEURS DE POLY(ADP-RIBOSE) GLYCOHYDROLASE ET UTILISATIONS DE CES COMPOSITIONS
  申请人：GUILFORD PHARM INC

  公开号：WO2000025787A1

  公开（公告）日：2000-05-11

  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 hydrochroride; 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.
• 1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) analogs: design, synthesis, anti-tumor and anti-oxidant activities
  作者：Qurat-ul-ain Shaikh、Meiting Yang、Khadim Hussain Memon、Mehreen Lateef、Du Na、Shengbiao Wan、Deslandes Eric、Lijuan Zhang、Tao Jiang

  DOI：10.1016/j.carres.2016.04.021

  日期：2016.7

  HT29 and H1299 cells with IC50 of 1.76 µM and 3.65 µM, respectively, indicating the mutual contribution of m-methoxy and p-hydroxy groups to the observed cytotoxicities. Moreover, cinnamic acid analogs were less active than the benzoic acid analogs evidenced by higher IC50 values. Furthermore, in cinnamic acid analogs the hydrogenation of double bond to saturated 2-C side chain enhance the cytotoxicities

  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