(E)-4-[2-(((4-(trifluoromethyl)phenyl)methyl)sulfinyl)-vinyl]benzene-1,2-diol | 1609008-05-0

• 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: (E)-4-[2-(((4-(trifluoromethyl)phenyl)methyl)sulfinyl)-vinyl]benzene-1,2-diol
• 英文别名: E-acetic acid 2-acetoxy-4-[2-(4-trifluoromethylphenylmethanesulfinyl)vinyl]phenyl ester；E-2-(3,4-dihydroxyphenyl)vinyl 4-trifluoromethylbenzyl sulfoxide；4-[(E)-2-[[4-(trifluoromethyl)phenyl]methylsulfinyl]ethenyl]benzene-1,2-diol
• CAS: 1609008-05-0
• 化学式: C₁₆H₁₃F₃O₃S
• 分子量: 342.339
• InChiKey: DBUVUORMXHCMTJ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-4-[2-(((4-(trifluoromethyl)phenyl)methyl)sulfinyl)-vinyl]benzene-1,2-diol 、 乙酸酐 在 吡啶 作用下， 以93%的产率得到E-acetic acid 2-acetoxy-4-[2-(4-trifluoromethylphenylmethanesulfinyl)vinyl]phenyl ester
  参考文献：
  名称：

  （E）-3,4-二乙酰氧基苯乙烯基砜和亚砜衍生物在帕金森氏病体外模型中的神经保护作用。

  摘要：

  （E）-3,4-二羟基苯乙烯基芳烷基砜和亚砜在先前的研究中已被报道为新型的多功能神经保护剂，它作为酚类化合物表现出抗氧化和抗炎的特性。为了进一步增强衍生物的神经保护作用和研究其构效关系，我们合成了它们的乙酰化衍生物，（E）-3,4-二乙酰氧基苯乙烯基砜和亚砜，并在体外帕金森氏病模型中检查了它们的神经保护作用。结果表明，（E）-3,4-二乙酰氧基苯乙烯基砜和亚砜可以显着抑制由6-OHDA，NO和H2O2等毒性引起的神经元细胞损伤。更重要的是，它们显示出更高的抗神经炎特性和与相应的未乙酰化化合物相似的抗氧化特性。因此，

  DOI：

  10.3109/14756366.2015.1037750
• 作为产物：
  描述：

  1-溴-三氟对二甲苯 在 四氢吡咯 、 双氧水 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (E)-4-[2-(((4-(trifluoromethyl)phenyl)methyl)sulfinyl)-vinyl]benzene-1,2-diol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of (E)-3,4-Dihydroxystyryl Aralkyl Sulfones and Sulfoxides as Novel Multifunctional Neuroprotective Agents

  摘要：

  Novel (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides were designed and synthesized as new analogues of 1, which showed interesting multifunctional neuroprotective effects, including antioxidative and antineuroinflammatory properties. Specifically, target compounds display excellent potency in scavenging reactive free radicals and demonstrate potent effects against various kinds of toxicities, including H2O2, 6-hydroxydopamine, and lipopolysaccharide in different types of neuronal cells. The antioxidative properties of the target compounds are more potent than that of 1, and the antineuroinflammatory properties are less strong than that of 1. According to the parallel artificial membrane permeation assay for the blood brain barrier, target compounds possess greater blood brain barrier (BBB) permeability than 1. In short, due to improvement of the antioxidative effect, stability, and BBB permeability, (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides can thus be considered as potential multifunctional neuroprotective agents and serve as new lead candidates in the treatment of neurodegenerative diseases.

  DOI：

  10.1021/jm500258v

文献信息

• Design, Synthesis, and Biological Evaluation of (<i>E</i>)-3,4-Dihydroxystyryl Aralkyl Sulfones and Sulfoxides as Novel Multifunctional Neuroprotective Agents
  作者：Xianling Ning、Ying Guo、Xiaowei Wang、Xiaoyan Ma、Chao Tian、Xueqi Shi、Renzong Zhu、Can Cheng、Yansheng Du、Zhizhong Ma、Zhili Zhang、Junyi Liu

  DOI：10.1021/jm500258v

  日期：2014.5.22

  Novel (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides were designed and synthesized as new analogues of 1, which showed interesting multifunctional neuroprotective effects, including antioxidative and antineuroinflammatory properties. Specifically, target compounds display excellent potency in scavenging reactive free radicals and demonstrate potent effects against various kinds of toxicities, including H2O2, 6-hydroxydopamine, and lipopolysaccharide in different types of neuronal cells. The antioxidative properties of the target compounds are more potent than that of 1, and the antineuroinflammatory properties are less strong than that of 1. According to the parallel artificial membrane permeation assay for the blood brain barrier, target compounds possess greater blood brain barrier (BBB) permeability than 1. In short, due to improvement of the antioxidative effect, stability, and BBB permeability, (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides can thus be considered as potential multifunctional neuroprotective agents and serve as new lead candidates in the treatment of neurodegenerative diseases.
• Neuroprotective effects of (<i>E</i>)-3,4-diacetoxystyryl sulfone and sulfoxide derivatives<i>in vitro</i>models of Parkinson's disease
  作者：Xianling Ning、Mengmeng Yuan、Ying Guo、Chao Tian、Xiaowei Wang、Zhili Zhang、Junyi Liu

  DOI：10.3109/14756366.2015.1037750

  日期：——

  sulfones and sulfoxides have been reported as novel multifunctional neuroprotective agents in previous studies, which as phenolic compounds display antioxidative and antineuroinflammatory properties. To further enhance the neuroprotective effects and study structure-activity relationship of the derivatives, we synthesized their acetylated derivatives, (E)-3,4-diacetoxystyryl sulfones and sulfoxides,

  （E）-3,4-二羟基苯乙烯基芳烷基砜和亚砜在先前的研究中已被报道为新型的多功能神经保护剂，它作为酚类化合物表现出抗氧化和抗炎的特性。为了进一步增强衍生物的神经保护作用和研究其构效关系，我们合成了它们的乙酰化衍生物，（E）-3,4-二乙酰氧基苯乙烯基砜和亚砜，并在体外帕金森氏病模型中检查了它们的神经保护作用。结果表明，（E）-3,4-二乙酰氧基苯乙烯基砜和亚砜可以显着抑制由6-OHDA，NO和H2O2等毒性引起的神经元细胞损伤。更重要的是，它们显示出更高的抗神经炎特性和与相应的未乙酰化化合物相似的抗氧化特性。因此，