1-{4-[3-(1,3-benzodioxol-5-ylmethoxy)propoxy]phenyl}ethanone | 1620544-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{4-[3-(1,3-benzodioxol-5-ylmethoxy)propoxy]phenyl}ethanone
• 英文别名: 1-[4-[3-(1,3-Benzodioxol-5-ylmethoxy)propoxy]phenyl]ethanone；1-[4-[3-(1,3-benzodioxol-5-ylmethoxy)propoxy]phenyl]ethanone
• CAS: 1620544-62-8
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: UQQCOUHBHJYQAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯乙酮 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 、 mineral oil 为溶剂， 反应 9.0h， 生成 1-{4-[3-(1,3-benzodioxol-5-ylmethoxy)propoxy]phenyl}ethanone
  参考文献：
  名称：

  Synthesis of new compounds with promising antiviral properties against group A and B Human Rhinoviruses

  摘要：

  The human common cold, which is a benign disease caused by the Rhinoviruses, generally receives palliative symptomatic treatments, since no specific therapy against any of these viruses currently exists. In this work, some original synthetic compounds were produced and tested, in order to find non-toxic substances with an improved protection index (PI) for infected cells, as compared to reference drugs such as Pirodavir. We designed a series of novel molecules with a double oxygen in the central hydrocarbon chain and some modifications of the lateral methylisoxazole and propoxybenzoate moieties of lead compound 6602 (ethyl 4-{3-[2-(3-methyl-1,2-isoxazol-5-yl)ethoxy]propoxy)benzoate). It was found that most of these substances were actually less toxic than Pirodavir; in addition, the new molecule indicated as 8c was more than 30 times less toxic than Pirodavir, about twice as active on the group A strain of Rhinovirus HRV14, and even four times more effective on the group B strain HRV39, as compared to Pirodavir's PI. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.05.066

文献信息

• Synthesis of new compounds with promising antiviral properties against group A and B Human Rhinoviruses
  作者：Angela M. Bernard、Maria G. Cabiddu、Stefania De Montis、Roberto Mura、Raffaello Pompei

  DOI：10.1016/j.bmc.2014.05.066

  日期：2014.8

  The human common cold, which is a benign disease caused by the Rhinoviruses, generally receives palliative symptomatic treatments, since no specific therapy against any of these viruses currently exists. In this work, some original synthetic compounds were produced and tested, in order to find non-toxic substances with an improved protection index (PI) for infected cells, as compared to reference drugs such as Pirodavir. We designed a series of novel molecules with a double oxygen in the central hydrocarbon chain and some modifications of the lateral methylisoxazole and propoxybenzoate moieties of lead compound 6602 (ethyl 4-3-[2-(3-methyl-1,2-isoxazol-5-yl)ethoxy]propoxy)benzoate). It was found that most of these substances were actually less toxic than Pirodavir; in addition, the new molecule indicated as 8c was more than 30 times less toxic than Pirodavir, about twice as active on the group A strain of Rhinovirus HRV14, and even four times more effective on the group B strain HRV39, as compared to Pirodavir's PI. (C) 2014 Elsevier Ltd. All rights reserved.