N-(4-biphenylacetanoyl)-L-homoserine lactone | 942296-32-4

• 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: N-(4-biphenylacetanoyl)-L-homoserine lactone
• 英文别名: N-(4-biphenyl)acetyl-L-homoserine lactone；N-[(3S)-2-oxooxolan-3-yl]-2-(4-phenylphenyl)acetamide
• CAS: 942296-32-4
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: NRIAMXCZWQOQQD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  C₃₅H₄₂Cl₂N₃O₈Pol 在 三氟乙酸 作用下， 反应 18.0h， 生成 N-(4-biphenylacetanoyl)-L-homoserine lactone
  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

• β‐Cyclodextrin Encapsulation of Synthetic AHLs: Drug Delivery Implications and Quorum‐Quenching Exploits
  作者：Eric W. Ziegler、Alan B. Brown、Nasri Nesnas、Christopher D. Chouinard、Anil K. Mehta、Andrew G. Palmer

  DOI：10.1002/cbic.202000773

  日期：2021.4.6

  A solution solution: Synthetic AHL analogues (SAHLAs) have demonstrated efficacy as quorum sensing inhibitors by receptor antagonism. However, like native AHLs, these compounds are poorly soluble. To improve their solubility, we investigated the association of three representative SAHLAs, and their hydrolysis products, with β‐cyclodextrin by spectrofluorimetry and evaluated co‐application of CDs with

  解决方案：合成 AHL 类似物 (SAHLA) 已通过受体拮抗作用证明作为群体感应抑制剂的功效。然而，与天然 AHL 一样，这些化合物的溶解性较差。为了提高它们的溶解度，我们通过荧光光谱法研究了三种代表性 SAHLA 及其水解产物与 β-环糊精的关联，并评估了 CD 与 SAHLA 在秀丽隐杆线虫感染模型中的共同应用。合成 AHL 的 β-环糊精封装（Palmer @FloridaTech）
• Modulation of Bacterial Quorum Sensing With Synthetic Ligands
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20200115356A1

  公开（公告）日：2020-04-16

  The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.
• MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20220411390A1

  公开（公告）日：2022-12-29

  The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.
• Efficient Synthesis and Evaluation of Quorum-Sensing Modulators Using Small Molecule Macroarrays
  作者：Thanit Praneenararat、Grant D. Geske、Helen E. Blackwell

  DOI：10.1021/ol901871y

  日期：2009.10.15

  A method for the synthesis of small molecule macroarrays of N-acylated l-homoserine lactones (AHLs) is reported. A focused library of AHLs was constructed, and the macroarray platform was found to be compatible with both solution and agar-overlay assays using quorum-sensing (QS) reporter strains. Several QS antagonists were discovered and serve to showcase the macroarray as a straightforward technique

  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。