bis(4-(trifluoromethyl)benzyl) diselenide | 1255907-88-0

• 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: bis(4-(trifluoromethyl)benzyl) diselenide
• 英文别名: 1-(Trifluoromethyl)-4-[[[4-(trifluoromethyl)phenyl]methyldiselanyl]methyl]benzene
• CAS: 1255907-88-0
• 化学式: C₁₆H₁₂F₆Se₂
• 分子量: 476.182
• InChiKey: YKSATEMCDQQFTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吲哚 、 bis(4-(trifluoromethyl)benzyl) diselenide 在 air 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以73%的产率得到3-((4-(trifluoromethyl)benzyl)selanyl)-1H-indole
  参考文献：
  名称：

  可见光促进无金属和光催化剂合成 3-硒吲哚和不对称二芳基硒化物†

  摘要：

  采用二有机基二硒化物和吲哚或富电子芳烃作为起始材料，开发了一种用于合成 3-硒吲哚的新颖且可持续的方法。在不使用过渡金属配合物或有机光催化剂作为敏化剂的情况下，使用可见蓝光来促进反应。不需要强氧化剂或碱等添加剂。此外，乙醇在温和的反应条件下被用作良性溶剂。通过这种简单且环保的方法，以良好至优异的分离产率获得了几种 3-硒吲哚和许多不对称二芳基硒化物。

  DOI：

  10.1039/c9ra03642c
• 作为产物：
  描述：

  1-溴-三氟对二甲苯 在 sodium tetrahydroborate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.0h， 生成 bis(4-(trifluoromethyl)benzyl) diselenide
  参考文献：
  名称：

  Selenocyanates and diselenides: A new class of potent antileishmanial agents

  摘要：

  Thirty five selenocyanate and diselenide compounds were subjected to in vitro screening against Leishmania infantum promastigotes and the most active ones were also tested in an axenic amastigote model. In order to establish the selectivity indexes (SI) the cytotoxic effect of each compound was also assayed against Jurkat and THP-1 cell lines.Thirteen derivatives exhibit better IC50 values than miltefosine and edelfosine. Bis(4-aminophenyl) diselenide exhibits the best activity when assayed in infected macrophages and one of the lowest cytotoxic activities against the human cell lines tested, with SI values of 32 and 24 against Jurkat and THP-1 cells, respectively. This compound thus represents a new lead for further studies aimed at establishing its mechanism of action. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.054

文献信息

• Silicon-Mediated Synthesis of Selenoaldehydes and Selenoacylsilanes and Their Hetero Diels–Alder Reactions
  作者：Alessandro Degl'Innocenti、Antonella Capperucci、Miriam Acciai、Caterina Tiberi

  DOI：10.1080/10426500902947989

  日期：2009.6.23

  Bis(trimethylsilyl)selenide (HMDSS) reacts efficiently with aldehydes in the presence of CoCl 2 .6H 2 O to afford selenoaldehydes, which are trapped as Diels–Alder adducts by different dienes. The reaction can be applied to acylsilanes, to afford selenoacylsilanes, isolated as their cycloadducts.

  双（三甲基甲硅烷基）硒化物 (HMDSS) 在 CoCl 2 .6H 2 O 的存在下与醛有效反应，得到硒醛，硒醛被不同的二烯以 Diels-Alder 加合物形式捕获。该反应可以应用于酰基硅烷，以提供硒酰基硅烷，作为它们的环加合物分离。
• Design, synthesis and antifungal activities of novel triazole derivatives with selenium-containing hydrophobic side chains
  作者：Meng-bi Guo、Zhong-zuo Yan、Xin Wang、Hang Xu、Chun Guo、Zhuang Hou、Ping Gong

  DOI：10.1016/j.bmcl.2022.129044

  日期：2022.12

  In this work, a series of novel 1,2,4-triazole derivatives with selenium-containing hydrophobic side chains were designed and synthesized based on the structure of lanosterol 14α-demethylase (CYP51). All compounds were characterized by HRMS, 1H NMR and 13C NMR. Then, their antifungal activities against eight human pathogenic fungi were evaluated in vitro by testing the minimal inhibitory concentrations

  本工作基于羊毛甾醇 14α-脱甲基酶 (CYP51) 的结构，设计并合成了一系列具有含硒疏水侧链的新型 1,2,4-三唑衍生物。所有化合物均通过 HRMS、1 H NMR和13 C NMR进行了表征。然后，在体外评估了它们对八种人类病原真菌的抗真菌活性通过测试最小抑菌浓度。结果表明，几乎所有测试的化合物被发现比对照药物氟康唑更有效地对抗所有测试的真菌菌株。进一步的机理研究表明，目标化合物具有真菌CYP51抑制活性。同时，代表性化合物显示出对哺乳动物细胞系的低细胞毒性作用。此外，对接结果表明，目标化合物与白色念珠菌CYP51 的结合模式优于氟康唑，尤其是在狭窄的疏水裂缝中。总的来说，可以进一步开发具有含硒疏水侧链的新型 1,2,4-三唑衍生物，用于治疗侵袭性真菌感染。
• Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light
  作者：Ignacio D. Lemir、Willber D. Castro-Godoy、Adrián A. Heredia、Luciana C. Schmidt、Juan E. Argüello

  DOI：10.1039/c9ra03642c

  日期：——

  the synthesis of 3-selenylindoles employing diorganyl diselenides and indoles or electron-rich arenes as starting materials. Visible blue light was used to promote the reaction without employing transition metal complexes or organic photocatalysts as sensitizers. Additives such as strong oxidants or bases were not required. Moreover, ethanol was employed as a benign solvent under mild reaction conditions

  采用二有机基二硒化物和吲哚或富电子芳烃作为起始材料，开发了一种用于合成 3-硒吲哚的新颖且可持续的方法。在不使用过渡金属配合物或有机光催化剂作为敏化剂的情况下，使用可见蓝光来促进反应。不需要强氧化剂或碱等添加剂。此外，乙醇在温和的反应条件下被用作良性溶剂。通过这种简单且环保的方法，以良好至优异的分离产率获得了几种 3-硒吲哚和许多不对称二芳基硒化物。
• Selenocyanates and diselenides: A new class of potent antileishmanial agents
  作者：Daniel Plano、Ylenia Baquedano、David Moreno-Mateos、María Font、Antonio Jiménez-Ruiz、Juan Antonio Palop、Carmen Sanmartín

  DOI：10.1016/j.ejmech.2011.04.054

  日期：2011.8

  Thirty five selenocyanate and diselenide compounds were subjected to in vitro screening against Leishmania infantum promastigotes and the most active ones were also tested in an axenic amastigote model. In order to establish the selectivity indexes (SI) the cytotoxic effect of each compound was also assayed against Jurkat and THP-1 cell lines.Thirteen derivatives exhibit better IC50 values than miltefosine and edelfosine. Bis(4-aminophenyl) diselenide exhibits the best activity when assayed in infected macrophages and one of the lowest cytotoxic activities against the human cell lines tested, with SI values of 32 and 24 against Jurkat and THP-1 cells, respectively. This compound thus represents a new lead for further studies aimed at establishing its mechanism of action. (C) 2011 Elsevier Masson SAS. All rights reserved.