2-[3′-hydroxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate | 1185745-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[3′-hydroxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate
• 英文别名: 2-[3'-hydroxy-4'-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]EtOAc；2-[4'-hydroxy-3'-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]EtOAc
• CAS: 1185745-16-7
• 化学式: C₂₃H₂₈O₁₃
• 分子量: 512.468
• InChiKey: DEHROJVGYSAQIM-YKZCJQPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  170.19
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-[3′-hydroxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以88%的产率得到2-(4-glucuronide-3-hydroxyphenyl)ethanol
  参考文献：
  名称：

  A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

  摘要：

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.016
• 作为产物：
  描述：

  3,4-二羟基苯乙醇醋酸 、 methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以51%的产率得到2-[3′-hydroxy-4′-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenyl]ethyl acetate
  参考文献：
  名称：

  A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

  摘要：

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.016

文献信息

• Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents
  作者：Efres Belmonte-Reche、Marta Martínez-García、Pablo Peñalver、Verónica Gómez-Pérez、Ricardo Lucas、Francisco Gamarro、José María Pérez-Victoria、Juan Carlos Morales

  DOI：10.1016/j.ejmech.2016.04.047

  日期：2016.8

  Existing treatments have considerable side effects and increase resistance of the parasites. We have measured antitrypanosomal and antileishmanial activity of natural phenols, tyrosol (TYR) and hydroxytyrosol (HT) and several of their esters and metabolites. We found significant IC50 values against Trypanosoma brucei for HT decanoate ester and HT dodecanoate ester (0.6 and 0.36 μM, respectively). This represents

  锥虫病和利什曼病一直是非洲国家健康和发展的真正挑战。现有疗法具有相当大的副作用并增加了寄生虫的抵抗力。我们已经测量了天然酚，酪醇（TYR）和羟基酪醇（HT）以及它们的一些酯和代谢物的抗胰锥虫和抗疟疾活性。我们发现针对布鲁氏锥虫的有效IC 50值用于HT癸酸酯和HT十二酸酯（分别为0.6和0.36μM）。这表示相对于HT的活性大大增加（分别为79和132倍）。此外，两种化合物均对非肿瘤性人类细胞系MRC-5（分别为118和106）表现出高选择性。然后，我们合成了一个有针对性的化合物库，以探索结构活性。我们发现HT癸酸酯和HT十二酸酯的醚和硫脲类似物在低微摩尔范围内也显示出针对布鲁氏杆菌的IC 50值。总之，二邻苯酚环和中等大小的烷基链对于活性至关重要，而它们之间化学键的性质似乎不太重要。
• Protective Activity of Hydroxytyrosol Metabolites on Erythrocyte Oxidative-Induced Hemolysis
  作者：Fátima Paiva-Martins、Aníbal Silva、Vasco Almeida、Mafalda Carvalheira、Cristina Serra、José Enrique Rodrígues-Borges、João Fernandes、Luis Belo、Alice Santos-Silva

  DOI：10.1021/jf4016202

  日期：2013.7.10

  The capacity of important hydroxytyrosol metabolites (homovanillyl alcohol, hydroxytyrosol acetate, homovanillyl alcohol acetate, hydroxytyrosol 3' and 4'-O-glucuronides, and homovanillyl alcohol 4'-O-glucuronide) to protect red blood cells (RBCs) from oxidative injury induced by the radical initiator 2,2'-azo-bis(2-amidinopropane) dihydrochloride (AAPH) or by the natural radical initiator H2O2 was evaluated. In the presence of AAPH, all compounds showed to protect RBCs from hemolysis in a dose-dependent manner, exccept for the homovanillyl alcohol glucuronide, with the order of activity being at 20 mu M hydroxytyrosol > hydroxytyrosol glucuronides = hydroxytyrosol acetate = homovanillyl alcohol = homovanillyl acetate > homovanillyl alcohol glucuronide. At 10 mu M, hydroxytyrosol, hydroxytyrosol acetate, and hydroxytyrosol glucuronides still protected hemoglobine from oxidation and from morphological RBC changes. In the presence of H2O2, hydroxytyrosol showed to significantly protect RBCs from oxidative hemolysis in a dose-dependent manner, but the hydroxytyrosol glucuronides showed only a limited protection that was independent of the concentration used.