(S)-2-(4-bromophenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(4-bromophenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide
• 英文别名: 2-(4-bromophenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide；N-(4-bromophenylacetanoyl)-L-homoserine lactone；N-(3-butyrolactone)-4-bromobenzeneacetamide；N-(4-bromo-phenylacetanoyl)-L-homoserine lactone；2-(4-bromophenyl)-N-[(3S)-2-oxooxolan-3-yl]acetamide
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: ARMCPRYGJUZWON-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5S)-5-aminooxolan-2-one;hydrobromide 在 三氟乙酸 作用下， 反应 18.0h， 生成 (S)-2-(4-bromophenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide
  参考文献：
  名称：

  使用小分子宏阵列有效合成和评估群体感应调制器

  摘要：

  报道了一种合成N-酰化l-高丝氨酸内酯 (AHL)小分子微阵列的方法。构建了一个重点 AHL 库，并发现宏阵列平台与使用群体感应 (QS) 报告菌株的溶液和琼脂覆盖测定兼容。发现了几种 QS 拮抗剂，并用于展示宏阵列作为 QS 研究的直接技术。

  DOI：

  10.1021/ol901871y

文献信息

• Small Molecule Inhibitors of Bacterial Quorum Sensing and Biofilm Formation
  作者：Grant D. Geske、Rachel J. Wezeman、Adam P. Siegel、Helen E. Blackwell

  DOI：10.1021/ja0530321

  日期：2005.9.1

  local population densities using small molecules (or autoinducers) in a process known as quorum sensing. Here, we report a new and efficient synthetic route to naturally occurring bacterial autoinducers [N-acyl l-homoserine lactones (AHLs)] that is readily amenable to the synthesis of analogues. This route has been applied in the first synthesis of a library of non-native AHLs. Evaluation of these compounds

  细菌在称为群体感应的过程中使用小分子（或自诱导剂）监测其局部种群密度。在这里，我们报告了一种新的、有效的天然细菌自体诱导剂 [N-酰基 l-高丝氨酸内酯 (AHL)] 的合成途径，该途径易于合成类似物。该路线已应用于非天然 AHL 库的首次合成。在细菌报告基因和生物膜测定中对这些化合物的评估揭示了一组有效的群体感应拮抗剂。这些配体将作为有价值的新工具来探索群体感应在细菌发病机制中的作用。
• Inhibition of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells by quorum sensing autoinducer-mimics
  作者：Bernardas Morkunas、Warren R. J. D. Galloway、Megan Wright、Brett M. Ibbeson、James T. Hodgkinson、Kieron M. G. O'Connell、Noemi Bartolucci、Martina Della Valle、Martin Welch、David R. Spring

  DOI：10.1039/c2ob26501j

  日期：——

  Pseudomonas aeruginosa is a notorious human pathogen associated with a range of life-threatening nosocomial infections. There is an increasing problem of antibiotic resistance in P. aeruginosa, highlighted by the emergence of multi-drug resistant strains. Thus the exploration of new strategies for the treatment of P. aeruginosa infections is clearly warranted. P. aeruginosa is known to produce a range of virulence factors that enhance its ability to damage the host tissue and cause disease. One of the most important virulence factors is pyocyanin. P. aeruginosa regulates pyocyanin production using an intercellular communication mechanism called quorum sensing, which is mediated by small signalling molecules termed autoinducers. One native autoinducer is N-(3-oxododecanoyl)-L-homoserine lactone (OdDHL). Herein we report the synthesis of a collection of abiotic OdDHL-mimics. A number of novel compounds capable of competing with the endogenous OdDHL and consequently, inhibiting the production of pyocyanin in cultures of wild type P. aeruginosa were identified. We present evidence suggesting that compounds of this general structural type act as direct antagonists of quorum sensing in P. aeruginosa and as such may find value as molecular tools for the study and manipulation of this signalling pathway. A direct quantitative comparison of the pyocyanin suppressive activities of the most active OdDHL-mimics with some previously-reported inhibitors (based around different general structural frameworks) of quorum sensing from the literature, was also made.

  铜绿假单胞菌是一种臭名昭著的人类病原体，与一系列危及生命的院内感染相关。铜绿假单胞菌对抗生素耐药性的问题日益严重，表现为多药耐药菌株的出现。因此，探索治疗铜绿假单胞菌感染的新策略显然是必要的。铜绿假单胞菌能够产生一系列毒力因子，增强其破坏宿主组织和引发疾病的能力。其中最重要的毒力因子之一是绿脓菌素。铜绿假单胞菌利用一种称为群体感应的细胞间通讯机制来调控绿脓菌素的产生，该机制由称为自诱导剂的小信号分子介导。一种天然的自诱导剂是N-(3-氧代十二烷酰)-L-高丝氨酸内酯（OdDHL）。在此我们报道了一系列非生物OdDHL模拟物的合成。我们鉴定出一些能够与内源性OdDHL竞争并因此抑制野生型铜绿假单胞菌培养物中绿脓菌素产生的新化合物。我们提供的证据表明，这种一般结构类型的化合物直接作为铜绿假单胞菌群体感应的拮抗剂，并且作为研究该信号途径的分子工具可能具有价值。我们还直接定量比较了活性最强的OdDHL模拟物与文献中报道的一些基于不同一般结构框架的群体感应抑制剂的绿脓菌素抑制活性。
• Electrochemical analysis of quorum sensing inhibition
  作者：Ohad Bukelman、Neri Amara、Roi Mashiach、Pnina Krief、Michael M. Meijler、Lital Alfonta

  DOI：10.1039/b901125k

  日期：——

  A one-step label-free electrochemical assay for quorum sensing inhibition in Pseudomonas aeruginosa is presented.

  介绍了一种抑制铜绿假单胞菌法定量感应的一步式无标记电化学检测方法。
• COVALENT INHIBITION OF BACTERIAL QUORUM SENSING
  申请人：The National Institute for Biotechnology in the Negev Ltd.

  公开号：US20140073690A1

  公开（公告）日：2014-03-13

  Inhibitors of bacterial communication, such as quorum sensing, and method of use and manufacture thereof.
• US9242951B2
  申请人：——

  公开号：US9242951B2

  公开（公告）日：2016-01-26