7,2',4',5'-四甲氧基黄酮 | 4253-02-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 7,2',4',5'-四甲氧基黄酮
• 英文名称: 7,2',4',5'-tetramethoxyisoflavone
• 英文别名: 2',4',5',7-Tetramethoxy-isoflavon；7-methoxy-3-(2,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 4253-02-5
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: LMCHYXAZXISBOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2914509090

反应信息

• 作为产物：
  描述：

  3-iodo-8,8-dimethylpyrano[2,3-f]chromen-4(8H)-one 在 palladium on activated charcoal 、 sodium carbonate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 7,2',4',5'-四甲氧基黄酮
  参考文献：
  名称：

  Synthesis, structure–activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents

  摘要：

  A series of barbigerone analogues (7a-7w, 13a-13x) were designed, synthesized and biologically evaluated for their anti-proliferative and anti-angiogenic activities. Among these compounds, compound 13a exhibited the most potent inhibitory effect on the proliferation of HUVECs, HepG2, A375, U251, B16, and HCT116 cells (IC50 = 3.80, 0.28, 1.58, 3.50, 1.09 and 0.68 mu M, respectively). Compound 13a inhibited the angiogenesis in zebrafish embryo assay in a concentration-dependent manner. Furthermore, 13a also effectively inhibited the migration and capillary like tube formation of human umbilical vein endothelial cell in vitro. These results support the further investigation of this class of compounds as potential anti-proliferative and anti-angiogenesis agents. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.04.121

文献信息

• Method of decreasing liquiritigenin-derived isoflavones relative to total isoflavones in plants and plants producing reduced ratio of liquiritigenin-derived isoflavones relative to total isoflavones
  申请人：——

  公开号：US20040128714A1

  公开（公告）日：2004-07-01

  This invention pertains to methods for decreasing the ratio of liquiritigenin-derived isoflavones relative to total isoflavone levels in isoflavonoid-producing plants and plant parts by transforming plants with a recombinant DNA construct comprising a nucleic acid sequence of at least 200 nucleotides and having at least 75% sequence identity to a polynucleotide encoding a chalcone reductase. More preferably, this invention pertains to methods for decreasing the ratios of daidzein and glycitein and their conjugates relative to total isoflavone levels in soybean plants and soybean plant parts by transforming plants with a recombinant DNA construct comprising a nucleic acid sequence of at least 200 nucleotides and having at least 75% sequence identity to a polynucleotide encoding a chalcone reductase.

  本发明涉及通过用重组 DNA 构建体转化植物来降低产生异黄酮的植物和植物部位中来源于利吉霉素的异黄酮相对于总异黄酮水平的比率的方法，该 DNA 构建体包含至少 200 个核苷酸的核酸序列，并且与编码查耳酮还原酶的多核苷酸具有至少 75% 的序列同一性。更优选地，本发明涉及通过用重组 DNA 构建体转化植物来降低大豆植物和大豆植物部位中的大豆异黄酮和甘草甜素及其共轭物相对于总异黄酮水平的比率的方法，该 DNA 构建体包含至少 200 个核苷酸的核酸序列，且与编码查尔酮还原酶的多核苷酸具有至少 75% 的序列同一性。
• US7323621B2
  申请人：——

  公开号：US7323621B2

  公开（公告）日：2008-01-29
• Synthesis, structure–activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents
  作者：Guangcheng Wang、Fang Wang、Dong Cao、Yibin Liu、Ronghong Zhang、Haoyu Ye、Xiuxia Li、Lin He、Zhuang Yang、Liang Ma、Aihua Peng、Mingli Xiang、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmcl.2014.04.121

  日期：2014.7

  A series of barbigerone analogues (7a-7w, 13a-13x) were designed, synthesized and biologically evaluated for their anti-proliferative and anti-angiogenic activities. Among these compounds, compound 13a exhibited the most potent inhibitory effect on the proliferation of HUVECs, HepG2, A375, U251, B16, and HCT116 cells (IC50 = 3.80, 0.28, 1.58, 3.50, 1.09 and 0.68 mu M, respectively). Compound 13a inhibited the angiogenesis in zebrafish embryo assay in a concentration-dependent manner. Furthermore, 13a also effectively inhibited the migration and capillary like tube formation of human umbilical vein endothelial cell in vitro. These results support the further investigation of this class of compounds as potential anti-proliferative and anti-angiogenesis agents. (C) 2014 Published by Elsevier Ltd.