4-(6-Methyl-1,3,6,2-dioxazaborocan-2-yl)phenol | 1420860-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(6-Methyl-1,3,6,2-dioxazaborocan-2-yl)phenol
• 英文别名: 4-(6-methyl-1,3,6,2-dioxazaborocan-2-yl)phenol
• CAS: 1420860-89-4
• 化学式: C₁₁H₁₆BNO₃
• 分子量: 221.064
• InChiKey: LEXUVRGIBNCVEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基二乙醇胺 、 4-羟基苯硼酸 以 甲苯 为溶剂， 反应 5.0h， 以55%的产率得到4-(6-Methyl-1,3,6,2-dioxazaborocan-2-yl)phenol
  参考文献：
  名称：

  Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi

  摘要：

  Two focused libraries based on two types of compounds, that is, thiazolidinediones and dioxazaborocanes were designed. Structural resemblances can be found between thiazolidinediones and well-known furanone type quorum sensing (QS) inhibitors such as N-acylaminofuranones, and/or acyl-homoserine lactone signaling molecules, while dioxazaborocanes structurally resemble previously reported oxazaborolidine derivatives which antagonized autoinducer 2 (AI-2) binding to its receptor. Because of this, we hypothesized that these compounds could affect AI-2 QS in Vibrio harveyi. Although all compounds blocked QS, the thiazolidinediones were the most active AI-2 QS inhibitors, with EC50 values in the low micromolar range. Their mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of V. harveyi QS mutants and by DNA-binding assays with purified LuxR protein. The active compounds neither affected bioluminescence as such nor the production of AI-2. Instead, our results indicate that the thiazolidinediones blocked AI-2 QS in V. harveyi by decreasing the DNA-binding ability of LuxR. In addition, several dioxazaborocanes were found to block AI-2 QS by targeting LuxPQ. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.055

文献信息

• Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi
  作者：Gilles Brackman、Abed Al Aziz Al Quntar、Claes D. Enk、Izet Karalic、Hans J. Nelis、Serge Van Calenbergh、Morris Srebnik、Tom Coenye

  DOI：10.1016/j.bmc.2012.11.055

  日期：2013.2

  Two focused libraries based on two types of compounds, that is, thiazolidinediones and dioxazaborocanes were designed. Structural resemblances can be found between thiazolidinediones and well-known furanone type quorum sensing (QS) inhibitors such as N-acylaminofuranones, and/or acyl-homoserine lactone signaling molecules, while dioxazaborocanes structurally resemble previously reported oxazaborolidine derivatives which antagonized autoinducer 2 (AI-2) binding to its receptor. Because of this, we hypothesized that these compounds could affect AI-2 QS in Vibrio harveyi. Although all compounds blocked QS, the thiazolidinediones were the most active AI-2 QS inhibitors, with EC50 values in the low micromolar range. Their mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of V. harveyi QS mutants and by DNA-binding assays with purified LuxR protein. The active compounds neither affected bioluminescence as such nor the production of AI-2. Instead, our results indicate that the thiazolidinediones blocked AI-2 QS in V. harveyi by decreasing the DNA-binding ability of LuxR. In addition, several dioxazaborocanes were found to block AI-2 QS by targeting LuxPQ. (C) 2012 Elsevier Ltd. All rights reserved.