3',5,5',6,7,8-hexamethoxyflavone | 70460-29-6

• 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: 3',5,5',6,7,8-hexamethoxyflavone
• 英文别名: 2-(3,5-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one；2-(3,5-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
• CAS: 70460-29-6
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: ADBLJUDPXDJMMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3',5'-dihydroxy-5,6,7,8-tetramethoxyflavone 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以76%的产率得到3',5,5',6,7,8-hexamethoxyflavone
  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.