2-diazo-3,4-dihydroxy-1-phenylbutan-1-one | 1370340-10-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 2-diazo-3,4-dihydroxy-1-phenylbutan-1-one
• 英文别名: (2E)-2-diazo-3,4-dihydroxy-1-phenylbutan-1-one
• CAS: 1370340-10-5
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: HZRFCNRDWRPVNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-diazo-3,4-dihydroxy-1-phenylbutan-1-one 在 二甲基二环氧乙烷 作用下， 生成 3,4-dihydroxy-1-phenylbutane-1,2-dione
  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
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 生成 2-diazo-3,4-dihydroxy-1-phenylbutan-1-one
  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

• Phosphorylated and Branched Dihydroxy-Pentane-Dione (DPD) Analogs as Quorum Sensing Inhibitors in Bacteria
  申请人：Sintim Herman

  公开号：US20120294900A1

  公开（公告）日：2012-11-22

  Provided are compositions and methods for modulating quorum sensing in microbes. The compounds are AI-2 analogs and as such have structures similar to 4,5-dihydroxy-2,3-pentanedione that can act as agonists/antagonists of quorum sensing. The compounds are useful for modulating quorum sensing in bacteria and can be used in methods for prophylaxis or therapy of bacterial infections and for reduction of biofilms.

  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。
• US8952192B2
  申请人：——

  公开号：US8952192B2

  公开（公告）日：2015-02-10
• Altering the Communication Networks of Multispecies Microbial Systems Using a Diverse Toolbox of AI-2 Analogues
  作者：Sonja Gamby、Varnika Roy、Min Guo、Jacqueline A. I. Smith、Jingxin Wang、Jessica E. Stewart、Xiao Wang、William E. Bentley、Herman O. Sintim

  DOI：10.1021/cb200524y

  日期：2012.6.15

  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.