| 1441774-75-9

• 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
• CAS: 1441774-75-9
• 化学式: C₁₈H₁₇FO₅
• 分子量: 332.328
• InChiKey: KOZZNLAERIXBOP-UHFFFAOYSA-N

物化性质

• 沸点：
  519.1±50.0 °C(predicted)
• 密度：
  1.256±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 双氧水 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以69%的产率得到7-fluoro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2′,4′,5′-trimethoxyflavonol derivatives as anti-inflammatory and antimicrobial agents

  摘要：

  A series of novel 3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (flavonol) derivatives (2a-u) of biological interest have been prepared via CLAISEN-SCHMIDT condensation followed by ALGAR-FLYNN-OYAMADA reaction and to search for the potent nonsteroidal anti-inflammatory agents from this novel series. All the synthesized compounds have been screened for their in vitro proinflammatory cytokines tumor necrosis factor (TNF-alpha) and interleukin-6 (IL-6) inhibitory activity along with antimicrobial activity. As many as three compounds viz. 2h, 2l, and 2q from this novel series were found to be potent TNF-alpha and IL-6 inhibitor (up to 72-81 % TNF-alpha and 86-92 % IL-6 inhibitory activity) but at 10 mu M concentration as compared with the standard dexamethasone (71 % TNF-alpha and 84 % IL-6 inhibitory activities at 1 mu M concentration). While the compounds 2d, 2m, 2n, and 2s were found to be potent antimicrobial agent showing even 2-2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL.

  DOI：

  10.1007/s00044-013-0651-z
• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲醛 、 4-氟-2-羟基苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2′,4′,5′-trimethoxyflavonol derivatives as anti-inflammatory and antimicrobial agents

  摘要：

  A series of novel 3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (flavonol) derivatives (2a-u) of biological interest have been prepared via CLAISEN-SCHMIDT condensation followed by ALGAR-FLYNN-OYAMADA reaction and to search for the potent nonsteroidal anti-inflammatory agents from this novel series. All the synthesized compounds have been screened for their in vitro proinflammatory cytokines tumor necrosis factor (TNF-alpha) and interleukin-6 (IL-6) inhibitory activity along with antimicrobial activity. As many as three compounds viz. 2h, 2l, and 2q from this novel series were found to be potent TNF-alpha and IL-6 inhibitor (up to 72-81 % TNF-alpha and 86-92 % IL-6 inhibitory activity) but at 10 mu M concentration as compared with the standard dexamethasone (71 % TNF-alpha and 84 % IL-6 inhibitory activities at 1 mu M concentration). While the compounds 2d, 2m, 2n, and 2s were found to be potent antimicrobial agent showing even 2-2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL.

  DOI：

  10.1007/s00044-013-0651-z