N-(2-{6-[2-acetamido-5-(trifluoromethyl)phenyl]pyridazin-3-yl}-4-(trifluoromethyl)phenyl)acetamide | 1276656-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(2-{6-[2-acetamido-5-(trifluoromethyl)phenyl]pyridazin-3-yl}-4-(trifluoromethyl)phenyl)acetamide
• 英文别名: N-[2-[6-[2-acetamido-5-(trifluoromethyl)phenyl]pyridazin-3-yl]-4-(trifluoromethyl)phenyl]acetamide
• CAS: 1276656-66-6
• 化学式: C₂₂H₁₆F₆N₄O₂
• 分子量: 482.385
• InChiKey: GKHCEWUVDPMSOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-氨基-5-三氟甲基苯硼酸频呐醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 碘 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-(2-{6-[2-acetamido-5-(trifluoromethyl)phenyl]pyridazin-3-yl}-4-(trifluoromethyl)phenyl)acetamide
  参考文献：
  名称：

  Synthetic Mimics of Antimicrobial Peptides from Triaryl Scaffolds

  摘要：

  In this report, we describe the synthesis of a new series of small amphiphilic aromatic compounds that mimic the essential properties of cationic antimicrobial peptides using Suzuki-Miyaura coupling. The new design allowed the easy tuning of the conformational restriction, controlled by introduction of intramolecular hydrogen bonds, and the overall hydrophobicity by modifications to the central ring and the side chains. This approach allowed us to better understand the influence of these features on the antimicrobial. activity and selectivity. We found that the overall hydrophobicity had a more significant impact on antimicrobial and hemolytic activity than the conformational stiffness. A novel compound was discovered which has MICs of 0.78 mu g/mL against S. Aureus and 6.25 mu g/mL against E. Coli, similar to the well-known antimicrobial peptide, MSI-78.

  DOI：

  10.1021/jm101410t

文献信息

• Synthetic Mimics of Antimicrobial Peptides from Triaryl Scaffolds
  作者：Hitesh D. Thaker、Federica Sgolastra、Dylan Clements、Richard W. Scott、Gregory N. Tew

  DOI：10.1021/jm101410t

  日期：2011.4.14

  In this report, we describe the synthesis of a new series of small amphiphilic aromatic compounds that mimic the essential properties of cationic antimicrobial peptides using Suzuki-Miyaura coupling. The new design allowed the easy tuning of the conformational restriction, controlled by introduction of intramolecular hydrogen bonds, and the overall hydrophobicity by modifications to the central ring and the side chains. This approach allowed us to better understand the influence of these features on the antimicrobial. activity and selectivity. We found that the overall hydrophobicity had a more significant impact on antimicrobial and hemolytic activity than the conformational stiffness. A novel compound was discovered which has MICs of 0.78 mu g/mL against S. Aureus and 6.25 mu g/mL against E. Coli, similar to the well-known antimicrobial peptide, MSI-78.