3-benzyl-3H-2-benzothiophen-1-one | 1351938-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyl-3H-2-benzothiophen-1-one
• CAS: 1351938-48-1
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: ZAKRJPYEWRNDJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (±)-3-benzyl-3-hydroxybenzo[c]thiophen-1(3H)-one 在 氢碘酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以62%的产率得到3-benzyl-3H-2-benzothiophen-1-one
  参考文献：
  名称：

  Discovery of a Potential Anti-Ischemic Stroke Agent: 3-Pentylbenzo[c]thiophen-1(3H)-one

  摘要：

  The development of novel antithrombotic agents with strong free radical scavenging activity is of great significance for the treatment of ischemic stroke. In the present study, 3-alkyl/arylalkyl-substituted benzo[c]thiophen-1(3H)-ones (5a-h) were designed and synthesized. The most active compound 5d significantly inhibited the adenosine diphosphate (ADP) induced and arachidonic acid (AA) induced in vitro platelet aggregation, superior to clinically used antiplatelet drug aspirin (ASP) and anti-ischemic stroke drugs 3-n-butylphthalide (NBP) and edaravone (Eda). More importantly, in comparison with both NBP and Eda, 5d exhibited stronger antithrombotic and free radical scavenging activities and better or comparable neuroprotective effects against ischemia/reperfusion (I/R) in rats by ameliorating neurobehavioral function, reducing infarct size and brain-water content, attenuating cerebral damage, and normalizing the levels of oxidative enzymes. Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents more potent than drugs like NBP and Eda.

  DOI：

  10.1021/jm300681r

文献信息

• Discovery of a Potential Anti-Ischemic Stroke Agent: 3-Pentylbenzo[<i>c</i>]thiophen-1(3<i>H</i>)-one
  作者：Jing Wu、Jingjing Ling、Xuliang Wang、Tingting Li、Jingchao Liu、Yisheng Lai、Hui Ji、Sixun Peng、Jide Tian、Yihua Zhang

  DOI：10.1021/jm300681r

  日期：2012.8.23

  The development of novel antithrombotic agents with strong free radical scavenging activity is of great significance for the treatment of ischemic stroke. In the present study, 3-alkyl/arylalkyl-substituted benzo[c]thiophen-1(3H)-ones (5a-h) were designed and synthesized. The most active compound 5d significantly inhibited the adenosine diphosphate (ADP) induced and arachidonic acid (AA) induced in vitro platelet aggregation, superior to clinically used antiplatelet drug aspirin (ASP) and anti-ischemic stroke drugs 3-n-butylphthalide (NBP) and edaravone (Eda). More importantly, in comparison with both NBP and Eda, 5d exhibited stronger antithrombotic and free radical scavenging activities and better or comparable neuroprotective effects against ischemia/reperfusion (I/R) in rats by ameliorating neurobehavioral function, reducing infarct size and brain-water content, attenuating cerebral damage, and normalizing the levels of oxidative enzymes. Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents more potent than drugs like NBP and Eda.