5-hydroxy-6,7,8,2',6'-pentamethoxyflavone | 99123-99-6

• 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: 5-hydroxy-6,7,8,2',6'-pentamethoxyflavone
• 英文别名: 2'-methoxyskullcapflavone II；2-(2,6-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxychromen-4-one
• CAS: 99123-99-6
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: FFSJMCTUMIHWJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 5,6,2',6'-tetrahydroxy-7,8-dimethoxyflavone 生成 5-hydroxy-6,7,8,2',6'-pentamethoxyflavone
  参考文献：
  名称：

  Studies on the nepalese crude drugs. XII. On the phenolic compounds from the root of Scutellaria prostrata JAcq. ex Benth.

  摘要：

  From the root of Scutellaria prostrata JACQ. ex BENTH., five compounds (I-V) were isolated, together with three known glycosides of phenylethanoid (IV-VIII) and sixteen known flavonoids (IX-XXIV). On the basis of chemical and spectral evidence, I-V were identified as 5, 6, 2', 6'-tetrahydroxy-7, 8-dimethoxyflavone, 5, 6, 2'-trihydroxy-7, 8, 6'-trimethoxyflavone, 5, 7, 2'-trihydroxy-8-methoxyflavone 7-O-β-D-glucuronopyranoside, 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-D-glucopyranoside and 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-D-(4-O-feruloyl)glucopyranoside, respectively. Compound II has already been synthesized.

  DOI：

  10.1248/cpb.39.1047

文献信息

• Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by flavonoids. II.
  作者：TAMOTSU NIKAIDO、TAICHI OHMOTO、USHIO SANKAWA、TSUYOSHI TOMIMORI、YUKINORI MIYAICHI、YOSHITAKA IMOTO

  DOI：10.1248/cpb.36.654

  日期：——

  Thirty-eight flavones obtained from Scutellaria baicalensis and ninety six related flavones were tested for inhibitory activity against adenosine 3', 5'-cyclic monophosphate phosphodiesterase from beef heart. The most active inhibitor is 8-methoxy-5, 7, 2'-trihydroxyflavone from S. baicalensis. Its IC50 value is 0.6(× 10-5 M/l). The structure-activity relationships were investigated. a) O-Methylated flavones generally show lower inhibitory activity than the corresponding hydroxyflavones among the flavones having under four substituents. b) O-Methylated flavones generally show higher inhibitory activity than the corresponding hydroxyflavones in the flavones having over five substituents. (c) C-Glycosides are almost all poor inhibitors. (d) O-Glycosides are generally less potent than the corresponding flavones.

  测试了从黄芩中提取的 38 种黄酮和 96 种相关黄酮对牛心腺苷 3'，5'-环单磷酸磷酸二酯酶的抑制活性。最有效的抑制剂是黄芩中的 8-甲氧基-5，7，2'-三羟基黄酮。其 IC50 值为 0.6(× 10-5 M/l)。a) 在四个取代基以下的黄酮类化合物中，O-甲基化黄酮的抑制活性通常低于相应的羟基黄酮。(c) C-糖苷几乎都是抑制效果较差的物质。(d) O-糖苷的抑制作用一般低于相应的黄酮。