(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-((4-(2-nitrophenyl)-4-oxobutyl)amino)-3-oxopropyl)-butanamide | 1401067-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2,4-dihydroxy-3,3-dimethyl-N-(3-((4-(2-nitrophenyl)-4-oxobutyl)amino)-3-oxopropyl)-butanamide
• 英文别名: (2R)-2,4-dihydroxy-3,3-dimethyl-N-[3-[[4-(2-nitrophenyl)-4-oxobutyl]amino]-3-oxopropyl]butanamide
• CAS: 1401067-54-6
• 化学式: C₁₉H₂₇N₃O₇
• 分子量: 409.439
• InChiKey: YJIHQJNKEPMABX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-3-(2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamido)propanoic acid 在 盐酸 、 4-羟基苯并三唑 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成 (R)-2,4-dihydroxy-3,3-dimethyl-N-(3-((4-(2-nitrophenyl)-4-oxobutyl)amino)-3-oxopropyl)-butanamide
  参考文献：
  名称：

  Validation of PqsD as an Anti-biofilm Target in Pseudomonas aeruginosa by Development of Small-Molecule Inhibitors

  摘要：

  2-Hepty1-4-hydroxyquinoline (HHQ) and Pseudomonas quinolone signal (PQS) are involved in the regulation of virulence factor production and biofilm formation in Pseudomonas aeruginosa. PqsD is a key enzyme in the biosynthesis of these signal molecules. Using a ligand-based approach, we have identified the first class of PqsD inhibitors. Simplification and rigidization led to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in P. aeruginosa. This validates PqsD as a target for the development of anti-infectives.

  DOI：

  10.1021/ja3072397

文献信息

• Validation of PqsD as an Anti-biofilm Target in Pseudomonas aeruginosa by Development of Small-Molecule Inhibitors
  作者：Michael P. Storz、Christine K. Maurer、Christina Zimmer、Nathalie Wagner、Christian Brengel、Johannes C. de Jong、Simon Lucas、Mathias Müsken、Susanne Häussler、Anke Steinbach、Rolf W. Hartmann

  DOI：10.1021/ja3072397

  日期：2012.10.3

  2-Hepty1-4-hydroxyquinoline (HHQ) and Pseudomonas quinolone signal (PQS) are involved in the regulation of virulence factor production and biofilm formation in Pseudomonas aeruginosa. PqsD is a key enzyme in the biosynthesis of these signal molecules. Using a ligand-based approach, we have identified the first class of PqsD inhibitors. Simplification and rigidization led to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in P. aeruginosa. This validates PqsD as a target for the development of anti-infectives.