7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one | 62252-32-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one
• 英文别名: 5,6-Dihydroxy-7-phenylmethoxy-2-(4-phenylmethoxyphenyl)chromen-4-one
• CAS: 62252-32-8
• 化学式: C₂₉H₂₂O₆
• 分子量: 466.49
• InChiKey: ZDPHRRIAEHONSA-UHFFFAOYSA-N

物化性质

• 沸点：
  712.9±60.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 高车前素
  参考文献：
  名称：

  Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo

  摘要：

  Scutellarin (1) could be hydrolyzed into scutellarein (2) in vivo and then converted into methylated, sulfated and glucuronidated forms. In order to investigate the biological activities of these methylated metabolites, eight methylated analogs of scutellarein (2) were synthesized via semi-synthetic methods. The antithrombotic activities of these compounds were evaluated through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity. Furthermore, the physicochemical properties of these compounds including aqueous solubility and lipophilicity were also investigated. The results showed that 6-O-methylscutellarein (5) demonstrated potent antithrombotic activity, stronger antioxidant activity and balanced solubility and permeability compared with scutellarin (1), which warrants further development of 5 as a promising lead for the treatment of ischemic cerebrovascular disease. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.039
• 作为产物：
  描述：

  红盏花素 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 42.0h， 生成 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  An Improved Synthesis of 6-O-Methyl-Scutellarein through Selective Benzylation

  摘要：

  本文描述了一种经改进的 6-O-甲基黄芩苷的合成方法。选择溴化苄基来保护黄芩苷中 C-4′ 和 C-7 的羟基。然后对产物进行甲基化和脱保护，通过四个步骤高产率地制备出目标化合物。

  DOI：

  10.3184/174751915x14452625043383

文献信息

• 一种6-甲基灯盏乙素苷元的制备方法
  申请人：南京中医药大学

  公开号：CN104311518B

  公开（公告）日：2016-07-13

  本发明涉及化学合成领域，具体涉及中药分子灯盏乙素活性代谢物的制备，将灯盏乙素在强酸作用下水解葡萄糖醛酸分子得到4’,5,6,7?四羟基黄酮，4’,5,6,7?四羟基黄酮与溴苄在缚酸剂存在下反应，生成5,6?二羟基?4’,7?二苄氧基黄酮，继而在碱性条件下与碘甲烷反应生成5?羟基?6?甲氧基?4’,7?二苄氧基黄酮，最后5?羟基?6?甲氧基?4’,7?二苄氧基黄酮在钯碳存在下催化氢化脱苄基得到6?甲基灯盏乙素苷元。本发明步骤简单，易纯化，条件温和，成本低，反应总收率大于70％，合成的产品纯度高，大于99.0％，适合工艺化生产。
• Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation
  作者：Min-Zhe Shen、Zhi-Hao Shi、Nian-Guang Li、Hao -Tang、Qian-Ping Shi、Yu-Ping Tang、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.2174/15701786113109990046

  日期：2013.11

  Scutellarin (1) possesses distinguished efficacy in the clinical therapy of cerebral infarction, coronary heart disease, and angina pectoris. Scutellarin (1) is readily converted in vivo, therefore, synthetic methods for the construction of its metabolites will be very important in the near future. In this work, an efficient and first synthetic method for 6-O-methyl- scutellarein (3), one metabolite of scutellarin in vivo, is developed. Dichlorodiphenylmethane in diphenyl ether is used firstly to protect the dihydroxy groups at C-6 and C-7 in scutellarein (2). Then, benzyl bromide is used to selectively protect the hydroxy groups at C-4' and C-7 in 10. 6-O-Methyl-scutellarein (3) is obtained in high yield through seven steps.

  黄芩苷（1）在脑梗塞、冠心病和心绞痛的临床治疗中具有显著疗效。黄芩苷（1）在体内很容易转化，因此，合成其代谢物的方法在不久的将来将非常重要。在这项工作中，首次开发出了黄芩苷的一种代谢物--6-O-甲基黄芩苷（3）的高效合成方法。首先用二苯醚中的二氯二苯甲烷保护黄芩苷（2）中 C-6 和 C-7 的二羟基。然后用溴化苄选择性地保护 10 中 C-4' 和 C-7 的羟基。通过七个步骤，便可高产获得 6-O-甲基黄芩苷（3）。