5-羟基-7-甲氧基-6-甲基-2-苯基色烯-4-酮 | 55969-57-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5-羟基-7-甲氧基-6-甲基-2-苯基色烯-4-酮
• 英文名称: 5-hydroxy-7-methoxy-6-methyl-2-phenyl-chromen-4-one
• 英文别名: 5-hydroxy-7-methoxy-6-methylflavone；5-hydroxy-6-methyl-7-methoxyflavone；6-Methyltectochrysin；5-hydroxy-7-methoxy-6-methyl-2-phenylchromen-4-one
• CAS: 55969-57-8
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: QXJMWAGIFVRLTO-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  176-179°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-羟基-7-甲氧基-6-甲基-2-苯基色烯-4-酮 、 乙酸酐 在 吡啶 作用下， 生成 5-acetoxy-7-methoxy-6-methyl-2-phenyl-chromen-4-one
  参考文献：
  名称：

  Mukerjee; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 38, p. 207,217

  摘要：

  DOI：
• 作为产物：
  描述：

  5-羟基-7-甲氧基-8-甲基-2-苯基色烯-4-酮 在 氢碘酸 、 乙酸酐 、 potassium carbonate 、 丙酮 作用下， 生成 5-羟基-7-甲氧基-6-甲基-2-苯基色烯-4-酮
  参考文献：
  名称：

  Mukerjee; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 38, p. 207,217

  摘要：

  DOI：

文献信息

• <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.
• Lindstedt; Misiorny, Acta Chemica Scandinavica (1947), 1951, vol. 5, p. 1,3
  作者：Lindstedt、Misiorny

  DOI：——

  日期：——
• Pillon; Mentzer, Bulletin de la Societe Chimique de France, 1954, p. 30,32
  作者：Pillon、Mentzer

  DOI：——

  日期：——
• Chopin; Justin, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 3307
  作者：Chopin、Justin

  DOI：——

  日期：——
• Anti-AIDS agents 68. The first total synthesis of a unique potent anti-HIV chalcone from genus Desmos
  作者：Kyoko Nakagawa-Goto、Kuo-Hsiung Lee

  DOI：10.1016/j.tetlet.2006.09.110

  日期：2006.11

  The first total synthesis of a unique highly functionalized and potent anti-HIV chalcone 1, isolated from genus Desmos, was achieved from commercially available 2,4,6-trihydroxytoluene (3) or 2,4,6-trihydroxybenzaldehyde (2) in five (from 3) or six steps (from 2). (c) 2006 Elsevier Ltd. All rights reserved.