6-bromo-8-methoxy-3-(pyridin-3-yl)coumarin | 52924-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-bromo-8-methoxy-3-(pyridin-3-yl)coumarin
• 英文别名: 8-Methoxy-6-brom-3-pyridylcumarin；6-bromo-8-methoxy-3-pyridin-3-yl-chromen-2-one；6-Bromo-8-methoxy-3-pyridin-3-ylchromen-2-one；6-bromo-8-methoxy-3-pyridin-3-ylchromen-2-one
• CAS: 52924-42-2
• 化学式: C₁₅H₁₀BrNO₃
• 分子量: 332.153
• InChiKey: FARZKDZBZFRWHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-吡啶乙酸 、 5-溴-2-羟基-3-甲氧基苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 8.0h， 以55%的产率得到6-bromo-8-methoxy-3-(pyridin-3-yl)coumarin
  参考文献：
  名称：

  3-Arylcoumarins: Synthesis and potent anti-inflammatory activity

  摘要：

  Chronic inflammation is the persistent and excessive immune response and can lead to a variety of diseases. Aiming to discover new compounds with anti-inflammatory activity, we report herein the synthesis and biological evaluation of 3-arylcoumarins. Thirty five 3-arylcoumarins were prepared through Perkin condensation and further acid-promoted hydrolysis if necessary. In lipopolysaccharide-activated mouse macrophage RAW264.7 cells, 6,8-dichloro-3-(2-methoxyphenyl) coumarin (16) and 6-bromo-8-methoxy-3-(3-methoxyphenyl) coumarin (25) exhibited nitric oxide production inhibitory activity with the IC50 values of 8.5 mu M and 6.9 mu M, respectively, providing a pharmacological potential as anti-inflammatory agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.033

文献信息

• 3-Arylcoumarins: Synthesis and potent anti-inflammatory activity
  作者：Wenchen Pu、Yuan Lin、Jianshuo Zhang、Fei Wang、Chun Wang、Guolin Zhang

  DOI：10.1016/j.bmcl.2014.10.033

  日期：2014.12

  Chronic inflammation is the persistent and excessive immune response and can lead to a variety of diseases. Aiming to discover new compounds with anti-inflammatory activity, we report herein the synthesis and biological evaluation of 3-arylcoumarins. Thirty five 3-arylcoumarins were prepared through Perkin condensation and further acid-promoted hydrolysis if necessary. In lipopolysaccharide-activated mouse macrophage RAW264.7 cells, 6,8-dichloro-3-(2-methoxyphenyl) coumarin (16) and 6-bromo-8-methoxy-3-(3-methoxyphenyl) coumarin (25) exhibited nitric oxide production inhibitory activity with the IC50 values of 8.5 mu M and 6.9 mu M, respectively, providing a pharmacological potential as anti-inflammatory agents. (C) 2014 Elsevier Ltd. All rights reserved.