1-(4-(benzo[d][1,3]dioxol-6-yloxy)phenyl)ethanone | 1019626-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(benzo[d][1,3]dioxol-6-yloxy)phenyl)ethanone
• 英文别名: 1-[4-(1,3-Benzodioxol-5-yloxy)phenyl]ethanone
• CAS: 1019626-70-0
• 化学式: C₁₅H₁₂O₄
• mdl: MFCD12622936
• 分子量: 256.258
• InChiKey: PRCWTYMOZJMXLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  5-氟靛红 、 1-(4-(benzo[d][1,3]dioxol-6-yloxy)phenyl)ethanone 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以50%的产率得到2-(4-(benzo[d][1,3]dioxol-6-yloxy)phenyl)-6-fluoroquinoline-4-carboxylic acid
  参考文献：
  名称：

  SAR-Based Optimization of a 4-Quinoline Carboxylic Acid Analogue with Potent Antiviral Activity

  摘要：

  It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-ctivity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl) quinoline -4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC50 of 1 nM and viral replication of VSV and WSN-Influenza with an EC50 of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogues of brequinar.

  DOI：

  10.1021/ml300464h
• 作为产物：
  描述：

  芝麻酚 、 4-碘代苯乙酮 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以33.7%的产率得到1-(4-(benzo[d][1,3]dioxol-6-yloxy)phenyl)ethanone
  参考文献：
  名称：

  SAR-Based Optimization of a 4-Quinoline Carboxylic Acid Analogue with Potent Antiviral Activity

  摘要：

  It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-ctivity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl) quinoline -4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC50 of 1 nM and viral replication of VSV and WSN-Influenza with an EC50 of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogues of brequinar.

  DOI：

  10.1021/ml300464h