5,7-dihydroxy-6,8-di-CC-prenylflavon | 50678-89-2

• 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: 5,7-dihydroxy-6,8-di-CC-prenylflavon
• 英文别名: 6,8-Di-DMA-chrysin；5,7-dihydroxy-6,8-bis(3-methylbut-2-enyl)-2-phenylchromen-4-one
• CAS: 50678-89-2
• 化学式: C₂₅H₂₆O₄
• 分子量: 390.479
• InChiKey: RGGJEENSFLRVRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白杨素 、 1-溴-3-甲基-2-丁烯 、 氨基钠 以2%的产率得到
  参考文献：
  名称：

  BEIRNE J. J.; CARROLL N. M.; OSULLIVAN W. I.; WOODS J., TETRAHEDRON , 1975, 31, NO 3, 265-267

  摘要：

  DOI：

文献信息

• Catalytic prenylation of natural polyphenols
  作者：Yi Du、Iman Korchi、Aleksandr E. Rubtsov、Andrei V. Malkov

  DOI：10.1039/d3nj04371a

  日期：——

  Prenylated polyphenols occur naturally and exhibit biological activity superior to the ubiquitous parent polyphenols. However, their low abundance limits the wider application of these derivatives. In this work, we present an expedient, single-step catalytic protocol for introducing terpene fragments into the aromatic rings of the widely available natural stilbenoids and flavonoids to upgrade their

  异戊二烯化多酚天然存在，并表现出优于普遍存在的母体多酚的生物活性。然而，它们的低丰度限制了这些衍生物的更广泛应用。在这项工作中，我们提出了一种便捷的单步催化方案，用于将萜烯片段引入广泛使用的天然二苯乙烯类化合物和黄酮类化合物的芳环中，以提高其治疗潜力。
• <i>C</i>-Isoprenylation of Flavonoids Enhances Binding Affinity toward P-Glycoprotein and Modulation of Cancer Cell Chemoresistance
  作者：Gilles Comte、Jean-Baptiste Daskiewicz、Christine Bayet、Gwenaëlle Conseil、Armelle Viornery-Vanier、Charles Dumontet、Attilio Di Pietro、Denis Barron

  DOI：10.1021/jm991128y

  日期：2001.3.1

  Previous studies have shown that flavones bind to P-glycoprotein (Pgp) with higher affinity than isoflavones, flavanones, and glycosylated derivatives. In the present work, a series of C- or O-substituted hydrophobic derivatives of chrysin were synthesized to further investigate structural requirements of the A ring toward Pgp modulation. Increasing hydrophobicity at either position 6, 8, or 7 increased the affinity of in vitro binding to a purified cytosolic domain of Pgp, but only benzyl and 3,3-dimethylallyl C-substitution produced a high maximal quenching of the protein intrinsic fluorescence. Inhibition of membrane Pgp within leukemic cells, characterized by intracellular drug accumulation, was specifically produced by isoprenylated derivatives, with 8-(3,3-dimethylallyl)chrysin being even more efficient than the commonly used cyclosporin A.