5,2'-dihydroxy-6,7,8-trimethoxyflavone | 86926-52-5

• 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: 5,2'-dihydroxy-6,7,8-trimethoxyflavone
• 英文别名: tenaxin I；5-hydroxy-2-(2-hydroxyphenyl)-6,7,8-trimethoxychromen-4-one
• CAS: 86926-52-5
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: QCKBVAGWPBRRQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,2'-dihydroxy-6,7,8-trimethoxyflavone 生成 5-hydroxy-6,7,8-trimethoxy-2-(2-methoxyphenyl)chromen-4-one
  参考文献：
  名称：

  RYU SUNG-HO;YOO BEONG-TAE;AHN BYUNG-ZUN,PACK MOO-YOUNG, ARCH. PHARM., 1985, 318, N 7, 659-661

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-benzyloxy-5,6,7,8-tetramethoxyflavone 在 三氯化硼 、 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 二氯甲烷 、 乙醇 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以82%的产率得到5,2'-dihydroxy-6,7,8-trimethoxyflavone
  参考文献：
  名称：

  Polymethoxyflavones as agents that prevent formation of cataract: Nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.10.133

文献信息

• RYU SUNG-HO;YOO BEONG-TAE;AHN BYUNG-ZUN,PACK MOO-YOUNG, ARCH. PHARM., 1985, 318, N 7, 659-661
  作者：RYU SUNG-HO、YOO BEONG-TAE、AHN BYUNG-ZUN,PACK MOO-YOUNG

  DOI：——

  日期：——
• 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.