B-[2-甲氧基-5-[(1E)-3-氧代-3-(3,4,5-三甲氧基苯基)-1-丙烯-1-基]苯基]硼酸 | 1215281-19-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: B-[2-甲氧基-5-[(1E)-3-氧代-3-(3,4,5-三甲氧基苯基)-1-丙烯-1-基]苯基]硼酸
• 英文名称: B-[2-methoxy-5-[(1E)-3-oxo-3-(3,4,5-trimethoxyphenyl)-1-propen-1-yl]phenyl]boronic acid
• 英文别名: YK-3-237；2-methoxy-5-[(1E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl]boronic acid；[2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl]boronic acid
• CAS: 1215281-19-8
• 化学式: C₁₉H₂₁BO₇
• 分子量: 372.183
• InChiKey: AKNGHUAJAODDJA-FNORWQNLSA-N

物化性质

• 沸点：
  616.2±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 5-醛基-2-甲氧基苯硼酸 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以63%的产率得到B-[2-甲氧基-5-[(1E)-3-氧代-3-(3,4,5-三甲氧基苯基)-1-丙烯-1-基]苯基]硼酸
  参考文献：
  名称：

  A boronic acid chalcone analog of combretastatin A-4 as a potent anti-proliferation agent

  摘要：

  Chalcones represent a class of natural products that inhibits tubulin assembly. In this study we designed and synthesized boronic acid analogs of chalcones in an effort to compare biological activities with combretastatin A-4, a potent inhibitor of tubulin polymerization. Systematic evaluation of the positional effects of the carbonyl moiety towards inhibition of tubulin polymerization, cancer cell proliferation and angiogenesis revealed that placement of the carbonyl adjacent to the trimethoxybenzene A-ring resulted in more active compounds than when the carbonyl group was placed adjacent to the C-ring. Our study identified a boronic acid chalcone with inhibition towards 16 human cancer cell lines in the 10-200 nM range, and another three cell lines with GI(50)-values below 10 nM. Furthermore, this drug has significant anti-angiogenesis effects demonstrated by HUVEC tube formation and aortic ring assay. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.003

文献信息

• A boronic acid chalcone analog of combretastatin A-4 as a potent anti-proliferation agent
  作者：Yali Kong、Kan Wang、Michael C. Edler、Ernest Hamel、Susan L. Mooberry、Mikell A. Paige、Milton L. Brown

  DOI：10.1016/j.bmc.2009.11.003

  日期：2010.1

  Chalcones represent a class of natural products that inhibits tubulin assembly. In this study we designed and synthesized boronic acid analogs of chalcones in an effort to compare biological activities with combretastatin A-4, a potent inhibitor of tubulin polymerization. Systematic evaluation of the positional effects of the carbonyl moiety towards inhibition of tubulin polymerization, cancer cell proliferation and angiogenesis revealed that placement of the carbonyl adjacent to the trimethoxybenzene A-ring resulted in more active compounds than when the carbonyl group was placed adjacent to the C-ring. Our study identified a boronic acid chalcone with inhibition towards 16 human cancer cell lines in the 10-200 nM range, and another three cell lines with GI(50)-values below 10 nM. Furthermore, this drug has significant anti-angiogenesis effects demonstrated by HUVEC tube formation and aortic ring assay. (C) 2009 Elsevier Ltd. All rights reserved.