methyl 2,3-di-O-galloyl-α-D-glucopyranoside | 81534-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-di-O-galloyl-α-D-glucopyranoside
• 英文别名: Methyl 2,3-di-O-galloyl-α-D-glucoside；2,3-digalloyl-1-O-methyl-α-D-glucose；galloyl(-2)[galloyl(-3)]a-Glc1Me；[(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-methoxy-5-(3,4,5-trihydroxybenzoyl)oxyoxan-4-yl] 3,4,5-trihydroxybenzoate
• CAS: 81534-37-4
• 化学式: C₂₁H₂₂O₁₄
• 分子量: 498.397
• InChiKey: UTEMCUTWDFVNEF-YCWNNZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  233
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  没食子酸甲酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 四丁基氟化铵 、 氢气 、 4-(dimethylamino)pyridine hydrochloride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 methyl 2,3-di-O-galloyl-α-D-glucopyranoside
  参考文献：
  名称：

  O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity

  摘要：

  The two anomers of O-methyl gluco-2,3-digalloyl esters were synthesized and their antimycotic activity toward yeasts of biomedical importance was evaluated. When used at subinhibitory concentration and regardless of stereochemistry at the anomeric carbon, these compounds enhance the antimycotic activity of Amphotericin B. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.037

文献信息

• The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides
  作者：Chang-Wei Li、Hua-Jin Dong、Cheng-Bin Cui

  DOI：10.3390/molecules20022034

  日期：——

  Twelve galloyl glucosides 1–12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-α-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-α-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-β-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-β-D-glucopyranose (1), 1,4,6-tri-O-galloyl-β-D-glucopyranose (2), 1,2-di-O-galloyl-β-D-glucopyranose (3), 1,3-di-O-galloyl-β-D-glucopyranose (4), 1,2,3-tri-O-galloyl-α-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-α-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1–12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 μg/mL, and their IC50 values were determined to be varied in 17.2–124.7 μM on the tested three human cancer cell lines. In addition, compounds 1–12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 μg/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.

  合成了十二种不同取代模式的鞣酸葡萄糖苷1–12，这些化合物含有两个或三个鞣酸基团，起始材料为商业可得的低成本D-葡萄糖和鞣酸。其中，三种化合物，即甲基3,6-二-O-鞣酸-α-D-葡萄糖吡喃苷（9）、乙基2,3-二-O-鞣酸-α-D-葡萄糖吡喃苷（11）和乙基2,3-二-O-鞣酸-β-D-葡萄糖吡喃苷（12）为新化合物，其余六种化合物，1,6-二-O-鞣酸-β-D-葡萄糖（1）、1,4,6-三-O-鞣酸-β-D-葡萄糖（2）、1,2-二-O-鞣酸-β-D-葡萄糖（3）、1,3-二-O-鞣酸-β-D-葡萄糖（4）、1,2,3-三-O-鞣酸-α-D-葡萄糖（6）和甲基3,4,6-三-O-鞣酸-α-D-葡萄糖吡喃苷（10），在本研究中首次合成。在体外MTT实验中，化合物1–12对人类癌细胞K562、HL-60和HeLa的抑制率在100 μg/mL时范围为64.2%至92.9%，其IC50值在测试的三种人类癌细胞系中变动为17.2–124.7 μM。此外，化合物1–12在体外MTT实验中对小鼠肉瘤S180细胞的抑制率在100 μg/mL时范围为38.7%至52.8%，并且在使用紫杉醇作为阳性对照的情况下，检测到化合物1和2在小鼠肉瘤S180肿瘤-bearing昆明小鼠中的体内抗肿瘤活性。
• Hydrolyzable Tannins with the Hexahydroxydiphenoyl Unit and the <i>m</i>-Depsidic Link:  HPLC-DAD-MS Identification and Model Synthesis
  作者：Panagiotis Arapitsas、Stefano Menichetti、Franco F. Vincieri、Annalisa Romani

  DOI：10.1021/jf0622329

  日期：2007.1.1

  This study was designed to develop efficient analytical tools for the difficult HPLC-DAD-MS identification of hydrolyzable tannins in natural tissue extracts. Throughout the study of the spectroscopic characteristics of properly synthesized stereodefined standards, it was observed that the UV-vis spectra of compounds with the m-depsidic link showed a characteristic shoulder at 300 nm, consistent with the simple glucogalloyl esters, whereas compounds with the hexahydroxydiphenoyl (HHDP) unit gave a diagnostic fragmentation pattern, caused by a spontaneous lactonization in the mass spectrometer. These observations were confirmed by HPLC-DAD-MS analyses of tannic acid and raspberry extracts, which are rich in hydrolyzable tannins with the m-depsidic link and the HHDP unit, respectively.
• O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity
  作者：Annalisa Romani、Stefano Menichetti、Panagiotis Arapitsas、Cristina Nativi、Benedetta Turchetti、Pietro Buzzini

  DOI：10.1016/j.bmcl.2005.06.037

  日期：2005.9

  The two anomers of O-methyl gluco-2,3-digalloyl esters were synthesized and their antimycotic activity toward yeasts of biomedical importance was evaluated. When used at subinhibitory concentration and regardless of stereochemistry at the anomeric carbon, these compounds enhance the antimycotic activity of Amphotericin B. (c) 2005 Elsevier Ltd. All rights reserved.