7-(benzyloxy)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one | 33507-92-5

• 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)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one
• 英文别名: 7-benzyloxy-5,6,4′-triacetoxyflavone；5,6-diacetoxy-2-(4-acetoxy-phenyl)-7-benzyloxy-chromen-4-one；[4-(5,6-Diacetyloxy-4-oxo-7-phenylmethoxychromen-2-yl)phenyl] acetate
• CAS: 33507-92-5
• 化学式: C₂₈H₂₂O₉
• 分子量: 502.477
• InChiKey: NFLWDRGHTPTRAI-UHFFFAOYSA-N

物化性质

• 熔点：
  190-193 °C(Solv: ethanol (64-17-5))
• 沸点：
  671.4±55.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one 在 甲醇 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 野黄芩素-7-甲基醚
  参考文献：
  名称：

  黄cut苷烷基衍生物的合成及其生物学评估，可预防脂质变性，改善神经退行性疾病。

  摘要：

  背景技术外源性抗氧化剂被认为是治疗神经退行性疾病的有前途的治疗方法，因为它们可以预防和/或最小化氧化引起的神经元损害。目的设计并合成了基于黄cut苷（2）的结构上的三系列亲脂性化合物，黄re苷（2）是黄cut苷（1）在体内的一种代谢产物。方法通过检测亚铁盐/抗坏血酸诱导的脂质自氧化产生的2-硫代巴比妥酸反应性物质（TBARS）来评估其抗氧化活性，所述脂质存在于大鼠肝细胞的微粒体膜中。用紫外（UV）分光光度计研究了表示为正辛醇和缓冲液之间分配系数的这些化合物的亲脂性。结果该研究表明在C4'-OH位置被苄基取代的化合物5e表现出强的抗氧化活性和良好的亲脂性。结论5e可能是预防或减少与神经退行性过程相关的氧化状态的有效候选者。

  DOI：

  10.2174/1573406414666181015143551
• 作为产物：
  描述：

  野黄芩素 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 7-(benzyloxy)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  黄cut苷烷基衍生物的合成及其生物学评估，可预防脂质变性，改善神经退行性疾病。

  摘要：

  背景技术外源性抗氧化剂被认为是治疗神经退行性疾病的有前途的治疗方法，因为它们可以预防和/或最小化氧化引起的神经元损害。目的设计并合成了基于黄cut苷（2）的结构上的三系列亲脂性化合物，黄re苷（2）是黄cut苷（1）在体内的一种代谢产物。方法通过检测亚铁盐/抗坏血酸诱导的脂质自氧化产生的2-硫代巴比妥酸反应性物质（TBARS）来评估其抗氧化活性，所述脂质存在于大鼠肝细胞的微粒体膜中。用紫外（UV）分光光度计研究了表示为正辛醇和缓冲液之间分配系数的这些化合物的亲脂性。结果该研究表明在C4'-OH位置被苄基取代的化合物5e表现出强的抗氧化活性和良好的亲脂性。结论5e可能是预防或减少与神经退行性过程相关的氧化状态的有效候选者。

  DOI：

  10.2174/1573406414666181015143551

文献信息

• METHOD FOR PREPARING HISPIDULIN AND ITS DERIVATIVES
  申请人：TAIPEI MEDICAL UNIVERSITY

  公开号：US20190322637A1

  公开（公告）日：2019-10-24

  Provided is a method for preparing hispidulin or a derivative thereof. The method includes selective protection of trihydroxybenzaldehyde, followed by regioselective iodination, selective protection, Stille coupling, Baeyer-Villiger oxidation and basic hydrolysis to obtain a protected intermediate compound. Then, alkylation, Claisen-Schmidt condensation, cyclization and deprotection of the protected intermediate compound are performed to obtain hispidulin or the derivative thereof. The present disclosure provides an efficient method for total synthesis of hispidulin or the derivative thereof with concise reaction steps and high yield.

  提供了一种制备hispidulin或其衍生物的方法。该方法包括选择性保护三羟基苯甲醛，然后进行选择性碘化、选择性保护、Stille偶联、Baeyer-Villiger氧化和碱性水解，以获得一种受保护的中间化合物。然后，进行烷基化、Claisen-Schmidt缩合、环化和去保护受保护中间化合物，以获得hispidulin或其衍生物。本公开提供了一种高效的hispidulin或其衍生物的全合成方法，具有简洁的反应步骤和高产率。
• An Improved Synthesis of Scutellarin-7-O-Glucuronid
  作者：Duo-Zhi Chen、Ting Wu、Zhao Zhao、Xi-Quan Lin、Tao Yang、Jian Yang

  DOI：10.3184/174751913x13813183192507

  日期：2013.11

  An eight-step synthesis of scutellarin-7-O-glucuronide via a novel preparation of the intermediate 5,6,7,4'-trimethoxyflavone from a chalcone derivative is described. The conditions of certain steps were studied and optimised to give an overall yield of 20%.
• Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo
  作者：Nian-Guang Li、Min-Zhe Shen、Zhen-Jiang Wang、Yu-Ping Tang、Zhi-Hao Shi、Yi-Fan Fu、Qian-Ping Shi、Hao Tang、Jian-Ao Duan

  DOI：10.1016/j.bmcl.2012.11.002

  日期：2013.1

  Based on metabolic mechanism of scutellarin in vivo that scutellarin could be hydrolyzed into scutellarein by beta-glucuronide enzyme, some glucose-containing scutellarein derivatives were designed and synthesized through the introduction of glucose moiety at C-7 position of scutellarein via a glucosidic bond. Biological activity evaluation showed that these glucose-containing scutellarein derivatives exhibited potent DPPH radical scavenging activities. Furthermore, the improvement of physicochemical properties such as anticoagulant and neuroprotective activities alongside with the water solubility was achieved by introducing glucose. These findings suggest that the introduction of the glucose moiety to scutellarein wattants further development of this kind of compounds as neuroprotective agents. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.