2-(4-(benzyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one | 1402607-46-8

• 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: 2-(4-(benzyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one
• CAS: 1402607-46-8
• 化学式: C₂₄H₂₀O₆
• 分子量: 404.419
• InChiKey: PIHGVZPNFXZDAB-UHFFFAOYSA-N

物化性质

• 沸点：
  617.4±55.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.13
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(4-(benzyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以0.21 g的产率得到蓟黄素
  参考文献：
  名称：

  Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes

  摘要：

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.034
• 作为产物：
  描述：

  α-(p-Benzyloxy-benzoyl)-6-hydroxy-2,3,4-trimethoxy-acetophenon 在 硫酸 、 三溴化硼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-(4-(benzyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one
  参考文献：
  名称：

  Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes

  摘要：

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.034

文献信息

• Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo
  作者：Zhi-Hao Shi、Nian-Guang Li、Zhen-Jiang Wang、Yu-Ping Tang、Ze-Xi Dong、Wei Zhang、Peng-Xuan Zhang、Ting Gu、Wen-Yu Wu、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.1016/j.ejmech.2015.10.039

  日期：2015.12

  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.