6-bromo-3-(3,4-dimethoxyphenyl)chromen-2-one

• 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: 6-bromo-3-(3,4-dimethoxyphenyl)chromen-2-one
• 英文别名: 6-bromo-3-(3,4-dimethoxyphenyl)-2H-chromen-2-one
• 化学式: C₁₇H₁₃BrO₄
• 分子量: 361.192
• InChiKey: VKHGGTDYQSPLFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-3-(3,4-dimethoxyphenyl)chromen-2-one 在 三溴化硼 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以81%的产率得到6-bromo-3-(3,4-dihydroxyphenyl)chromen-2-one
  参考文献：
  名称：

  Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity

  摘要：

  In the present project, a series of coumarin analogues, were synthesised and evaluated for their antioxidant and soybean lipoxygenase inhibitory activity. A variety of structural modifications on the coumarin scaffold revealed interesting structure-activity relationships concerning the different biological assays. Prenyloxy-coumarins 9 and 10 displayed the best combined inhibition of lipid peroxidation and soybean lipoxygenase. Thiocoumarins 11 and 14 were identified as potent lipoxygenase inhibitors whereas hydrazone analogues 15 and 16 were efficient DPPH radical scavengers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.008
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 、 5-溴水杨醛 在 N,N'-羰基二咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以49%的产率得到6-bromo-3-(3,4-dimethoxyphenyl)chromen-2-one
  参考文献：
  名称：

  Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity

  摘要：

  In the present project, a series of coumarin analogues, were synthesised and evaluated for their antioxidant and soybean lipoxygenase inhibitory activity. A variety of structural modifications on the coumarin scaffold revealed interesting structure-activity relationships concerning the different biological assays. Prenyloxy-coumarins 9 and 10 displayed the best combined inhibition of lipid peroxidation and soybean lipoxygenase. Thiocoumarins 11 and 14 were identified as potent lipoxygenase inhibitors whereas hydrazone analogues 15 and 16 were efficient DPPH radical scavengers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.008

文献信息

• Ultrasound-Assisted Solvent-Free Parallel Synthesis of 3-Arylcoumarins Using <i>N</i>-Acylbenzotriazoles
  作者：Sirawit Wet-osot、Chuthamat Duangkamol、Wong Phakhodee、Mookda Pattarawarapan

  DOI：10.1021/acscombsci.6b00055

  日期：2016.6.13

  An ultrasound-assisted one-pot acylation/cyclization reaction between N-acylbenzotriazoles and 2-hydroxybenzaldehydes has been developed for the synthesis of substituted 3-arylcoumarins. Using ultrasound not only allows rapid and clean conversion but also simplifies experimental setup and parallel workup leading to rapid generation of 3-arylcoumarin libraries under mild, solvent-free, and chromatography-free

  已经开发了N-酰基苯并三唑与2-羟基苯甲醛之间的超声辅助一锅酰化/环化反应，用于合成取代的3-芳基香豆素。使用超声波不仅可以实现快速，清洁的转化，而且可以简化实验设置和并行处理，从而在温和，无溶剂和无色谱的条件下快速生成3-芳基香豆素文库。
• Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity
  作者：Marina Roussaki、Konstantinos Zelianaios、Eleni Kavetsou、Stylianos Hamilakis、Dimitra Hadjipavlou-Litina、Christos Kontogiorgis、Thalia Liargkova、Anastasia Detsi

  DOI：10.1016/j.bmc.2014.10.008

  日期：2014.12

  In the present project, a series of coumarin analogues, were synthesised and evaluated for their antioxidant and soybean lipoxygenase inhibitory activity. A variety of structural modifications on the coumarin scaffold revealed interesting structure-activity relationships concerning the different biological assays. Prenyloxy-coumarins 9 and 10 displayed the best combined inhibition of lipid peroxidation and soybean lipoxygenase. Thiocoumarins 11 and 14 were identified as potent lipoxygenase inhibitors whereas hydrazone analogues 15 and 16 were efficient DPPH radical scavengers. (C) 2014 Elsevier Ltd. All rights reserved.