2-((3-Fluorobenzyl)oxy)benzonitrile | 898736-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((3-Fluorobenzyl)oxy)benzonitrile
• 英文别名: 2-[(3-fluorophenyl)methoxy]benzonitrile
• CAS: 898736-02-2
• 化学式: C₁₄H₁₀FNO
• mdl: MFCD11127438
• 分子量: 227.238
• InChiKey: NLVZKTRDEPCKHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻羟基苯甲腈 、 间氟氯苄 在 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 生成 2-((3-Fluorobenzyl)oxy)benzonitrile
  参考文献：
  名称：

  Ginger and Its Bioactive Component Inhibit Enterotoxigenic Escherichia coli Heat-Labile Enterotoxin-Induced Diarrhea in Mice

  摘要：

  Ginger is one of the most commonly used fresh herbs and spices. Enterotoxigenic Escherichia coli heat-labile enterotoxin (LT)-induced diarrhea is the leading cause of infant death in developing countries. In this study, we demonstrated that ginger significantly blocked the binding of LT to cell-surface receptor G(M1), resulting in the inhibition of fluid accumulation in the closed ileal loops of mice. Biological-activity-guided searching for active components showed that zingerone (vanillylacetone) was the likely active constituent responsible for the antidiarrheal efficacy of ginger. Further analysis of chemically synthesized zingerone derivatives revealed that compound 31 (2-[(4-methoxybenzyl)oxy]benzoic acid) significantly suppressed LT-induced diarrhea in mice via an excellent surface complementarity with the B subunits of LT. In conclusion, our findings provide evidence that ginger and its derivatives may be effective herbal supplements for the clinical treatment of enterotoxigenic Escherichia coli diarrhea.

  DOI：

  10.1021/jf071460f

文献信息

• Ginger and Its Bioactive Component Inhibit Enterotoxigenic <i>Escherichia coli</i> Heat-Labile Enterotoxin-Induced Diarrhea in Mice
  作者：Jaw-Chyun Chen、Li-Jiau Huang、Shih-Lu Wu、Sheng-Chu Kuo、Tin-Yun Ho、Chien-Yun Hsiang

  DOI：10.1021/jf071460f

  日期：2007.10.1

  Ginger is one of the most commonly used fresh herbs and spices. Enterotoxigenic Escherichia coli heat-labile enterotoxin (LT)-induced diarrhea is the leading cause of infant death in developing countries. In this study, we demonstrated that ginger significantly blocked the binding of LT to cell-surface receptor G(M1), resulting in the inhibition of fluid accumulation in the closed ileal loops of mice. Biological-activity-guided searching for active components showed that zingerone (vanillylacetone) was the likely active constituent responsible for the antidiarrheal efficacy of ginger. Further analysis of chemically synthesized zingerone derivatives revealed that compound 31 (2-[(4-methoxybenzyl)oxy]benzoic acid) significantly suppressed LT-induced diarrhea in mice via an excellent surface complementarity with the B subunits of LT. In conclusion, our findings provide evidence that ginger and its derivatives may be effective herbal supplements for the clinical treatment of enterotoxigenic Escherichia coli diarrhea.