2,6-di-tert-butyl-4-selenocyanatophenol | 97490-50-1

• 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: 2,6-di-tert-butyl-4-selenocyanatophenol
• 英文别名: 2,6-Di-t-butyl-4-selenocyanatophenol；(3,5-ditert-butyl-4-hydroxyphenyl) selenocyanate
• CAS: 97490-50-1
• 化学式: C₁₅H₂₁NOSe
• 分子量: 310.298
• InChiKey: BNVYOYCGEWSOGX-UHFFFAOYSA-N

物化性质

• 沸点：
  354.7±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-di-tert-butyl-4-selenocyanatophenol 在 锌 作用下， 以 甲醇 为溶剂， 生成 <1-Hydroxy-2,6-di-tert.-butyl>-selenophenol-(4)
  参考文献：
  名称：

  Mueller,E. et al., Justus Liebigs Annalen der Chemie, 1962, vol. 657, p. 5 - 12

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二叔丁基苯酚 、 potassium selenocyanate 在 溴 、 potassium bromide 作用下， 以 甲醇 为溶剂， 生成 2,6-di-tert-butyl-4-selenocyanatophenol
  参考文献：
  名称：

  Mueller,E. et al., Justus Liebigs Annalen der Chemie, 1962, vol. 657, p. 5 - 12

  摘要：

  DOI：

文献信息

• Design, Synthesis, and In Vitro Evaluation of a Novel Probucol Derivative: Protective Activity in Neuronal Cells Through GPx Upregulation
  作者：Ruth Liliám Quispe、Rômulo Faria Santos Canto、Michael Lorenz Jaramillo、Flavio Augusto Rocha Barbosa、Antônio Luiz Braga、Andreza Fabro de Bem、Marcelo Farina

  DOI：10.1007/s12035-018-0939-6

  日期：2018.10

  Recent studies have shown that probucol (PB), a hipocholesterolemic agent with antioxidant and anti-inflammatory properties, presents neuroprotective properties. On the other hand, adverse effects have limited PB’s clinical application. Thus, the search for PB derivatives with no or less adverse effects has been a topic of research. In this study, we present a novel organoselenium PB derivative (RC513) and investigate its potential protective activity in an in vitro experimental model of oxidative toxicity induced by tert-butyl hydroperoxide (tBuOOH) in HT22 neuronal cells, as well as exploit potential protective mechanisms. tBuOOH exposure caused a significant decrease in the cell viability, which was preceded by (i) increased reactive species generation and (ii) decreased mitochondrial maximum oxygen consumption rate. RC513 pretreatment (48 h) significantly prevented the tBuOOH-induced decrease of cell viability, RS generation, and mitochondrial dysfunction. Of note, RC513 significantly increased glutathione peroxidase (GPx) activity and mRNA expression of GPx1, a key enzyme involved in peroxide detoxification. The use of mercaptosuccinic acid, an inhibitor of GPx, significantly decreased the protective activity of RC513 against tBuOOH-induced cytotoxicity in HT22 cells, highlighting the importance of GPx upregulation in the observed protection. In summary, the results showed a significant protective activity of a novel PB derivative against tBuOOH-induced oxidative stress and mitochondrial dysfunction, which was related to the upregulation of GPx. Our results point to RC513 as a promising neuroprotective molecule, even though studies concerning potential beneficial effects and safety aspects of RC513 under in vivo conditions are well warranted.

  最近的研究表明，普布可（PB）是一种具有抗氧化和抗炎特性的降胆固醇剂，表现出神经保护特性。然而，副作用限制了PB的临床应用。因此，寻找无或少副作用的PB衍生物一直是研究的主题。在本研究中，我们提出了一种新型有机硒PB衍生物（RC513），并研究其在由叔丁基过氧化氢（tBuOOH）诱导的HT22神经元细胞氧化毒性体外实验模型中的潜在保护活性，并探讨潜在的保护机制。tBuOOH暴露导致细胞活力显著下降，伴随（i）活性物质生成增加和（ii）线粒体最大氧消耗率下降。RC513预处理（48小时）显著防止了tBuOOH诱导的细胞活力下降、活性物质生成增加及线粒体功能障碍。值得注意的是，RC513显著增加了谷胱甘肽过氧化物酶（GPx）活性及GPx1的mRNA表达，GPx是参与过氧化物解毒的关键酶。使用GPx抑制剂—巯基琥珀酸对RC513抵御tBuOOH诱导的HT22细胞细胞毒性的保护活性产生了显著降低，强调了GPx上调在观察到的保护中的重要性。总之，结果显示新型PB衍生物对tBuOOH诱导的氧化应激和线粒体功能障碍具有显著的保护活性，这与GPx的上调相关。我们的结果表明RC513是一种有前景的神经保护分子，尽管在体内条件下关于RC513潜在益处和安全性的研究仍然非常必要。
• New Probucol Analogues Inhibit Ferroptosis, Improve Mitochondrial Parameters, and Induce Glutathione Peroxidase in HT22 Cells
  作者：Diones Caeran Bueno、Rômulo Faria Santos Canto、Viviane de Souza、Rafaela Rafognatto Andreguetti、Flávio Augusto Rocha Barbosa、Aline Aita Naime、Partha Narayan Dey、Verena Wüllner、Mark William Lopes、Antônio Luiz Braga、Axel Methner、Marcelo Farina

  DOI：10.1007/s12035-020-01956-9

  日期：2020.8

  effects in vivo. We now describe the design and synthesis of two new probucol analogues that protect against glutamate-induced oxidative cell death, also known as ferroptosis, in cultured mouse hippocampal (HT22) cells and in primary cortical neurons, while probucol did not show any protective effect. Treatment with both compounds did not affect glutathione depletion but still significantly decreased glutamate-induced

  普罗布考是一种降胆固醇化合物，在几种神经退行性疾病模型中具有神经保护作用，但在体内具有严重的副作用。我们现在描述了两种新的普罗布考类似物的设计和合成，这些类似物在培养的小鼠海马 (HT22) 细胞和原代皮层神经元中防止谷氨酸诱导的氧化细胞死亡，也称为铁死亡，而普罗布考没有显示出任何保护作用。用这两种化合物处理不影响谷胱甘肽的消耗，但仍显着降低谷氨酸诱导的氧化剂产生、线粒体超氧化物的产生和 HT22 细胞中的线粒体超极化。这两种化合物都增加了谷胱甘肽过氧化物酶 (GPx) 1 的水平和 GPx 活性，还表现出对 RSL3（一种 GPx4 灭活剂）的保护作用。
• COMPOSITIONS AND METHODS FOR TREATING CARDIOVASCULAR DISORDERS
  申请人：Stocker Roland O.

  公开号：US20100004333A1

  公开（公告）日：2010-01-07

  The present invention relates to compounds and methods for the treatment of cardiovascular diseases and disorders. Compounds according to the present invention may comprise an optionally substituted phenyl ring linked to an aromatic or alkyl group by a spacer, wherein the spacer comprises two groups selected from selenium, sulfur, S(O) and S(O) 2 and may further optionally comprise an alkylene, alkenylene, cycloalkylene or arylene moiety between the respective selenium, sulfur, S(O) and S(O) 2 groups.

  本发明涉及化合物和方法，用于治疗心血管疾病和紊乱。根据本发明的化合物可能包括一个可选取代的苯环，通过一个间隔连接到一个芳香族或烷基团，其中该间隔包括从硒，硫，S（O）和S（O）2中选择的两个基团，并且还可以在各自的硒，硫，S（O）和S（O）2基团之间进一步选择包括一个烷基，烯基，环烷基或芳基的基团。
• WO2006/63408
  申请人：——

  公开号：——

  公开（公告）日：——