(±)-3-hexyl-3-hydroxybenzo[c]thiophen-1(3H)-one

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (±)-3-hexyl-3-hydroxybenzo[c]thiophen-1(3H)-one
• 英文别名: 3-Hexyl-3-hydroxy-2-benzothiophen-1-one；3-hexyl-3-hydroxy-2-benzothiophen-1-one
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: NGZLPWMKJZBDEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-3-hexyl-3-hydroxybenzo[c]thiophen-1(3H)-one 在 氢碘酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以59%的产率得到3-hexyl-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
• 作为产物：
  描述：

  苯酐 在 sodiumsulfide nonahydrate 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 (±)-3-hexyl-3-hydroxybenzo[c]thiophen-1(3H)-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

• Unexpected rearrangements in the synthesis of arylidene- or alkylidene-2-thiophthalides
  作者：Harald Paulussen、Peter Adriaensens、Dirk Vanderzande、Jan Gelan

  DOI：10.1016/0040-4020(96)00678-3

  日期：1996.9

  to suitable quinoid model compounds for PITN. Within this context benzylidenedithiophthalide and pentylidenedithiophthalide were chosen as target molecules. The unexpected rearrangements and the control of these rearrangements in the synthesis of benzylidenedithiophthalide and pentylidenedithiophthalide are reported.

  关于通过将市售单体与五硫化二磷（P 4 S 10）反应，一步合成聚（异硫杂萘）（PITN）的反应的机理研究，就产生了一种合成链终止分子的想法，该链终止分子应产生适用于PITN的醌型模型化合物。在这种情况下，选择苄基二硫代邻苯二甲酰和戊二烯二硫代邻苯二甲酸酯作为靶分子。报道了苄二烯二噻吩和戊二烯二噻吩的合成中意想不到的重排和这些重排的控制。