3',5,6,7,8-pentamethoxyflavone | 73909-62-3

• 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: 3',5,6,7,8-pentamethoxyflavone
• 英文别名: 5,6,7,8-tetramethoxy-2-(3-methoxyphenyl)chromen-4-one
• CAS: 73909-62-3
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: VGGCDYAXGPXIHL-UHFFFAOYSA-N

物化性质

• 沸点：
  565.3±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 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：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-苯甲氧基苯甲酰氯 在 4-二甲氨基吡啶 、 20% palladium hydroxide on charcoal 、 potassium tert-butylate 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 16.0h， 生成 3',5,6,7,8-pentamethoxyflavone
  参考文献：
  名称：

  B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production

  摘要：

  Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-alpha-stimulated human lens epithelial cells, the 2'-hydroxylated analogue 5a exerted marked inhibitory effects (IC50: 0.4 mu M) on PMA-treated cells, which were 170-fold more potent than those on TNF-alpha-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.001

文献信息

• B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production
  作者：Tetsuta Oshitari、Yuji Okuyama、Yoshiki Miyata、Hiroshi Kosano、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1016/j.bmc.2011.10.001

  日期：2011.12

  Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-alpha-stimulated human lens epithelial cells, the 2'-hydroxylated analogue 5a exerted marked inhibitory effects (IC50: 0.4 mu M) on PMA-treated cells, which were 170-fold more potent than those on TNF-alpha-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9. (C) 2011 Elsevier Ltd. All rights reserved.