7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one | 29096-94-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one
• 英文别名: 7-hydroxy-2',4',5'-trimethoxyisoflavone；7-hydroxy-3-(2,4,5-trimethoxy-phenyl)-chromen-4-one；7-hydroxy-3-(2,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 29096-94-4
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: IXZYJZHCXHSCDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 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：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 在 氢碘酸 作用下， 反应 2.0h， 以38.8%的产率得到2',4',5',7-tetrahydroxyisoflavone
  参考文献：
  名称：

  Nishiyama, Kiyotoshi; Esaki, Sachiko; Deguchi, Ikuko, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 1, p. 107 - 114

  摘要：

  DOI：
• 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 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 生成 7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one
  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

• Pathak, V. P.; Saini, T. R.; Khanna, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 89 - 90
  作者：Pathak, V. P.、Saini, T. R.、Khanna, R. N.

  DOI：——

  日期：——
• Nishiyama, Kiyotoshi; Esaki, Sachiko; Deguchi, Ikuko, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 1, p. 107 - 114
  作者：Nishiyama, Kiyotoshi、Esaki, Sachiko、Deguchi, Ikuko、Sugiyama, Naoko、Kamiya, Shintaro

  DOI：——

  日期：——
• 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.