2'-benzyloxy-5,6,7,8-tetramethoxyflavone | 1350827-42-7

• 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: 2'-benzyloxy-5,6,7,8-tetramethoxyflavone
• CAS: 1350827-42-7
• 化学式: C₂₆H₂₄O₇
• 分子量: 448.472
• InChiKey: DZBHONRXRXZBMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76.36
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2'-benzyloxy-5,6,7,8-tetramethoxyflavone 在 20% palladium hydroxide on charcoal 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2',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
• 作为产物：
  描述：

  2-(2-benzyloxybenzoyloxy)-3,4,5,6-tetramethoxyacetophenone 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.0h， 生成 2'-benzyloxy-5,6,7,8-tetramethoxyflavone
  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

• Polymethoxyflavones as agents that prevent formation of cataract: Nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells
  作者：Yoshiki Miyata、Tetsuta Oshitari、Yuji Okuyama、Arata Shimada、Hideyo Takahashi、Hideaki Natsugari、Hiroshi Kosano

  DOI：10.1016/j.bmcl.2012.10.133

  日期：2013.1

  Posterior capsular opacification (PCO) is the most frequent complication and the primary reason for visual decrease after extracapsular cataract surgery. The proliferation and migration of leftover lens epithelial cells (LECs) after surgery may contribute to the development of PCO. To prevent PCO, a rational approach would be to inhibit both the proliferation and the migration of LECs using nontoxic xenobiotics. Nobiletin, one of the most abundant polymethoxyflavones (PMFs) in citrus peel, and its synthetic congeners displayed a potent inhibition of LEC proliferation. Structural features which enhance anti-proliferative activity have also been discussed. (C) 2012 Elsevier Ltd. All rights reserved.