7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde | 412027-80-6

• 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-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde
• 英文别名: 7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde；7-Hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromen-6-carbaldehyd；7-Hydroxy-5-methoxy-6-formyl-flavon；7-Hydroxy-5-methoxy-4-oxo-2-phenylchromene-6-carbaldehyde
• CAS: 412027-80-6
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: YACBBEGDZRCDGC-UHFFFAOYSA-N

物化性质

• 熔点：
  207 °C(Solv: ethanol (64-17-5))
• 沸点：
  547.0±50.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde 在 盐酸 、 sodium hydroxide 、 双氧水 作用下， 生成 黄芩素
  参考文献：
  名称：

  Furo-chromones and -Coumarins. XII. Synthesis of Fraxinol from Bergapten and of Baicalein from Visnagin

  摘要：

  DOI：

  10.1021/ja01625a055
• 作为产物：
  描述：

  5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基- 在 potassium dichromate 、 硫酸 作用下， 生成 7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde
  参考文献：
  名称：

  某些取代的呋喃色酮，苯并呋喃和黄酮衍生物的合成和抗惊厥活性。

  摘要：

  合成了呋喃色酮，2-苯基色酮（黄酮）和被硫代氨基脲或噻唑烷丁-4-酮取代的苯并呋喃衍生物。分别以丙戊酸和苯妥英钠为参考标准，对所有新合成的化合物在皮下戊四氮诱发的癫痫发作（scPTZ）和最大电击诱发的癫痫发作（MES）试验中均进行了抗惊厥活性的测试。scPTZ模型中活性最高的化合物为1c，2b，5a和7e，在腹膜内给药时在300 mg / kg时显示出100％的保护作用。此外，研究了三种活性最高的化合物（1c，2b，5a）的预处理对小鼠4-氨基吡啶诱导的致死性的影响。用这些化合物进行预处理显着增加了阵挛性和强直性惊厥的潜伏期，并防止了4-氨基吡啶诱发的死亡。因此，这提供了这些化合物的抗惊厥活性和对它们的神经保护活性的证据。基于获得的数据研究了构效关系。

  DOI：

  10.1248/cpb.58.1148

文献信息

• Design, synthesis and structure–activity relationship of novel semi-synthetic flavonoids as antiproliferative agents
  作者：F.A. Ragab、T.A.A. Yahya、M.M. El-Naa、R.K. Arafa

  DOI：10.1016/j.ejmech.2014.06.007

  日期：2014.7

  Various flavonoid scaffold based derivatives viz furochalcones (3a-e, 6a-d and 9a-d), furoflavones (10a-d, 11a-d,12a-d,18a&b), flavones (21a-d), furoaurones (13a,b,14a-d and 15a-d) and 7-styrylfurochromones (22a-d and 25a-e) were designed and synthesized. The novel compounds were evaluated for their anti-proliferative activity against a panel of 60 cancer cell lines comprising 9 types of tumors. Ten compounds belonging to the major subgroups of flavonoids viz furochalcones (3a, 3d, 6b, 9a and 9b), furoflavones (12a and 12c), furoaurones (15d), styrylfurochromones (25b and 25e) showed very promising activity. These active compounds were also evaluated in vitro as kinase inhibitors against CDK2/cyclin E1, CDK4/cyclin D1 and GSK-3 beta and the best inhibition was displayed against GSK-3 beta with the allylfurochalcone derivative 9b exhibiting 80% decrease in GSK-3 beta catalytic activity. On the other hand, the styrylfurochromone 25e interestingly showed a 13% enhancement of GSK-3 beta catalytic power and a 12% reduction in CDK4/cyclin D1 activity. Finally, the in vivo anti-tumor activity of 25e was evaluated against breast cancer induced in mice. The results showed a profound anti-tumor effect of 25e that accompanies a significant increase and decrease in the levels of GSK-3 beta and cyclin D1, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.