3-acetyl-1,3-bis[4-nitro-2-(trifluoromethyl)phenyl]triazene | 1313389-47-7

• 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: 3-acetyl-1,3-bis[4-nitro-2-(trifluoromethyl)phenyl]triazene
• 英文别名: N-[4-nitro-2-(trifluoromethyl)phenyl]-N-[[4-nitro-2-(trifluoromethyl)phenyl]diazenyl]acetamide
• CAS: 1313389-47-7
• 化学式: C₁₆H₉F₆N₅O₅
• 分子量: 465.268
• InChiKey: DWLKFVBTLTUXED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1,3-bis(4-nitro-2-(trifluoromethyl)phenyl)triazene 、 乙酰氯 在 三乙胺 作用下， 生成 3-acetyl-1,3-bis[4-nitro-2-(trifluoromethyl)phenyl]triazene
  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

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.