2,3-Difluoro-4,5-dihydroxy-benzaldehyde | 426226-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-Difluoro-4,5-dihydroxy-benzaldehyde
• 英文别名: 2,3-Difluoro-4,5-dihydroxybenzaldehyde
• CAS: 426226-77-9
• 化学式: C₇H₄F₂O₃
• 分子量: 174.104
• InChiKey: BPRFVTSMTWMAEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-Difluoro-4,5-dihydroxy-benzaldehyde 在 barium hydroxide octahydrate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-3-[2,3-Difluoro-4,5-bis-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(2,4-dimethoxy-phenyl)-propenone
  参考文献：
  名称：

  Synthesis and biological activities of fluorinated chalcone derivatives

  摘要：

  We have designed and synthesized new 5-lipoxygenase inhibitors, fluorinated 3,4-dihydroxychalcones, and evaluated their biological activities with respect to antiperoxidation activity and in vitro antitumor activities. All fluorinated chalcones tested showed 5-lipoxygenase inhibition on rat basophilic leukemia-1 (RBL-1) cells and inhibitory action on Fe3+ -ADP induced NADPH-dependent lipid peroxidation in rat liver microsomes. The potencies were comparable or better to that of the lead 3,4-dihydroxychalcone. 6-Fluoro-3,4-dihydroxy-2',4'-dimethoxy chalcone (7) was the most effective compound in the in vitro assay using a human cancer cell line panel (HCC panel) consisting of 39 systems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00319-4

文献信息

• Synthesis and biological activities of fluorinated chalcone derivatives
  作者：Chika Nakamura、Nobuhide Kawasaki、Hideki Miyataka、Ezhuthachan Jayachandran、In Ho Kim、Kenneth L Kirk、Takeo Taguchi、Yoshio Takeuchi、Hitoshi Hori、Toshio Satoh

  DOI：10.1016/s0968-0896(01)00319-4

  日期：2002.3

  We have designed and synthesized new 5-lipoxygenase inhibitors, fluorinated 3,4-dihydroxychalcones, and evaluated their biological activities with respect to antiperoxidation activity and in vitro antitumor activities. All fluorinated chalcones tested showed 5-lipoxygenase inhibition on rat basophilic leukemia-1 (RBL-1) cells and inhibitory action on Fe3+ -ADP induced NADPH-dependent lipid peroxidation in rat liver microsomes. The potencies were comparable or better to that of the lead 3,4-dihydroxychalcone. 6-Fluoro-3,4-dihydroxy-2',4'-dimethoxy chalcone (7) was the most effective compound in the in vitro assay using a human cancer cell line panel (HCC panel) consisting of 39 systems. (C) 2002 Elsevier Science Ltd. All rights reserved.