1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triazene | 1243357-92-7

• 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: 1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triazene
• 英文别名: 4-nitro-N-[(E)-[4-nitro-2-(trifluoromethyl)phenyl]azo]-2-(trifluoromethyl)aniline；4-nitro-N-[[4-nitro-2-(trifluoromethyl)phenyl]diazenyl]-2-(trifluoromethyl)aniline
• CAS: 1243357-92-7
• 化学式: C₁₄H₇F₆N₅O₄
• 分子量: 423.231
• InChiKey: ZTUFOYDYQIKXSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triazene 在 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 以93%的产率得到potassium 1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triaz-2-en-1-ide
  参考文献：
  名称：

  Diaryltriazenes as antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA) and Mycobacterium smegmatis

  摘要：

  Diaryltriazene derivatives were synthesized and evaluated for their antimicrobial properties. Initial experiments showed some of these compounds to have activity against both methicillin-resistant strains of Staphylococus aureus (MRSA) and Mycobacterium smegmatis, with MICs of 0.02 and 0.03 mu g/mL respectively. Those compounds with potent anti-staphylococcal and anti-mycobacterial activity were not found to act as growth inhibitors of mammalian cell lines or yeast. Furthermore, we demonstrated that one of the most active anti-MRSA diaryltriazene derivatives was subject to very low frequencies of resistance at <10(-9). Whole genome sequencing of resistant isolates identified mutations in the enzyme that lysylates phospholipids. This could result in the modification of phospholipid metabolism and consequently the characteristics of the staphylococcal cell membrane, ultimately modifying the sensitivity of these pathogens to triazene challenge. Our work has therefore extended the potential range of triazenes, which could yield novel antimicrobials with low levels of resistance. Crown Copyright (C) 2016 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.12.060
• 作为产物：
  描述：

  2-氨基-5-硝基三氟甲苯 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 48.0h， 以68%的产率得到1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triazene
  参考文献：
  名称：

  新型强效抗肿瘤药4-硝基取代的1,3-二芳基三氮烯的合成与生物学评价

  摘要：

  我们描述了一种新型的1,3-二芳基三氮烯，即4-硝基取代的1,3-二芳基三氮烯的合成和生物活性。结构-活性关系分析表明，可以通过在苯环对位引入两个硝基和两个附加的吸电子基团（溴，氯，三氟甲基或氟）将1，3-二芳基三氮烯从无活性转变为具有高细胞毒性的化合物。取代基）在其邻位。为了增加改性化合物的溶解度，我们向其三氮烯氮中引入了各种酰基。LC-MS / MS分析的结果表明，N-酰基三氮烯可以被认为是非酰化的三氮烯的前药。选定的3-乙酰基1,3-双（2-氯-4-硝基苯基）-1-三氮烯（8b）对不同的肿瘤细胞系（包括顺铂耐药的喉癌细胞）具有高度的细胞毒性。值得注意的是，它对肿瘤细胞的抗增殖活性明显高于对正常细胞的抗增殖活性。DNA结合分析表明8b或其未酰化衍生物8a均未结合到DNA的小沟中。取而代之的是，8b会诱导活性氧，从而激发内质网（ER a）应激，最终导致细胞凋亡。我们的数据表明4-硝基取代

  DOI：

  10.1016/j.ejmech.2011.04.024

文献信息

• Diaryltriazenes as antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA) and Mycobacterium smegmatis
  作者：Jure Vajs、Conor Proud、Anamaria Brozovic、Martin Gazvoda、Adrian Lloyd、David I. Roper、Maja Osmak、Janez Košmrlj、Christopher G. Dowson

  DOI：10.1016/j.ejmech.2016.12.060

  日期：2017.2

  Diaryltriazene derivatives were synthesized and evaluated for their antimicrobial properties. Initial experiments showed some of these compounds to have activity against both methicillin-resistant strains of Staphylococus aureus (MRSA) and Mycobacterium smegmatis, with MICs of 0.02 and 0.03 mu g/mL respectively. Those compounds with potent anti-staphylococcal and anti-mycobacterial activity were not found to act as growth inhibitors of mammalian cell lines or yeast. Furthermore, we demonstrated that one of the most active anti-MRSA diaryltriazene derivatives was subject to very low frequencies of resistance at <10(-9). Whole genome sequencing of resistant isolates identified mutations in the enzyme that lysylates phospholipids. This could result in the modification of phospholipid metabolism and consequently the characteristics of the staphylococcal cell membrane, ultimately modifying the sensitivity of these pathogens to triazene challenge. Our work has therefore extended the potential range of triazenes, which could yield novel antimicrobials with low levels of resistance. Crown Copyright (C) 2016 Published by Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of 4-nitro-substituted 1,3-diaryltriazenes as a novel class of potent antitumor agents
  作者：Tamara Čimbora-Zovko、Anamaria Brozovic、Ivo Piantanida、Gerhard Fritz、Andrej Virag、Branko Alič、Vita Majce、Marijan Kočevar、Slovenko Polanc、Maja Osmak

  DOI：10.1016/j.ejmech.2011.04.024

  日期：2011.7

  We describe the synthesis and biological activity of a new class of 1,3-diaryltriazenes, namely 4-nitro-substituted 1,3-diaryltriazenes. Structure–activity relationship analysis reveals that 1,3-diaryltriazenes can be modified from inactive to highly cytotoxic compounds by the introduction of two nitro groups at the para positions of benzene rings and two additional electron-withdrawing groups (bromo

  我们描述了一种新型的1,3-二芳基三氮烯，即4-硝基取代的1,3-二芳基三氮烯的合成和生物活性。结构-活性关系分析表明，可以通过在苯环对位引入两个硝基和两个附加的吸电子基团（溴，氯，三氟甲基或氟）将1，3-二芳基三氮烯从无活性转变为具有高细胞毒性的化合物。取代基）在其邻位。为了增加改性化合物的溶解度，我们向其三氮烯氮中引入了各种酰基。LC-MS / MS分析的结果表明，N-酰基三氮烯可以被认为是非酰化的三氮烯的前药。选定的3-乙酰基1,3-双（2-氯-4-硝基苯基）-1-三氮烯（8b）对不同的肿瘤细胞系（包括顺铂耐药的喉癌细胞）具有高度的细胞毒性。值得注意的是，它对肿瘤细胞的抗增殖活性明显高于对正常细胞的抗增殖活性。DNA结合分析表明8b或其未酰化衍生物8a均未结合到DNA的小沟中。取而代之的是，8b会诱导活性氧，从而激发内质网（ER a）应激，最终导致细胞凋亡。我们的数据表明4-硝基取代