cyclobutyl-DPD | 1370339-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclobutyl-DPD
• 英文别名: 1-Cyclobutyl-3,4-dihydroxybutane-1,2-dione；1-cyclobutyl-3,4-dihydroxybutane-1,2-dione
• CAS: 1370339-97-1
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: QEFVPOWFTBRKDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclobutyl-DPD 、 邻苯二胺 反应 0.17h， 生成 1-(3-cyclobutylquinoxalin-2-yl)ethane-1,2-diol
  参考文献：
  名称：

  Phosphorylated and Branched Dihydroxy-Pentane-Dione (DPD) Analogs as Quorum Sensing Inhibitors in Bacteria

  摘要：

  提供了一种调节微生物群体感应的组合物和方法。这些化合物是AI-2类似物，因此具有类似于4,5-二羟基-2,3-戊二酮的结构，可以作为微生物群体感应的激动剂/拮抗剂。这些化合物对调节细菌的群体感应很有用，并可用于预防或治疗细菌感染以及减少生物膜的方法中。

  公开号：

  US20120294900A1
• 作为产物：
  描述：

  1-cyclobutyl-2-diazo-3,4-dihydroxybutan-1-one 在 二甲基二环氧乙烷 作用下， 生成 cyclobutyl-DPD
  参考文献：
  名称：

  Altering the Communication Networks of Multispecies Microbial Systems Using a Diverse Toolbox of AI-2 Analogues

  摘要：

  There have been intensive efforts to find small molecule antagonists for bacterial quorum sensing (QS) mediated by the "universal" QS autoinducer, AI-2. Previous work has shown that linear and branched aryl analogues of AI-2 can selectively modulate AI-2 signaling in bacteria. Additionally, LsrK-dependent phosphorylated analogues have been implicated as the active inhibitory form against AI-2 signaling. We used these observations to synthesize an expanded and diverse array of AI-2 analogues, which included aromatic as well as cyclic C-1-alkyl analogues. Species-specific analogues that disrupted AI-2 signaling in Escherichia coli and Salmonella typhimurium were identified. Similarly, analogues that disrupted QS behaviors in Pseudomonas aeruginosa were found. Moreover, we observed a strong correlation between LsrK-dependent phosphorylation of these acyl analogues and their ability to suppress QS. Significantly, we demonstrate that these analogues can selectively antagonize QS in single bacterial strains in a physiologically relevant polymicrobial culture.

  DOI：

  10.1021/cb200524y

文献信息

• US8952192B2
  申请人：——

  公开号：US8952192B2

  公开（公告）日：2015-02-10