I(2)-Oxo-N-(tetrahydro-2-oxo-3-furanyl)benzenebutanamide | 929222-23-1

• 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: I(2)-Oxo-N-(tetrahydro-2-oxo-3-furanyl)benzenebutanamide
• 英文别名: 3-oxo-N-(2-oxooxolan-3-yl)-4-phenylbutanamide
• CAS: 929222-23-1
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: SZKJWOMSLREKNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 I(2)-Oxo-N-(tetrahydro-2-oxo-3-furanyl)benzenebutanamide
  参考文献：
  名称：

  New synthetic analogues of N-acyl homoserine lactones as agonists or antagonists of transcriptional regulators involved in bacterial quorum sensing

  摘要：

  A series of 22 novel synthetic N-acyl-homoserine lactone analogues has been evaluated for both their inducing activity and their ability to competitively inhibit the action of 3-oxo-hexanol-L-homoserine lactone. the natural inducer of bioluminescence in the bacterium Vibrio fischeri. In the newly synthesized analogues, the extremity of the acyl chain was modified by introducing ramified alkyl, cycloalkyl or aryl substituents at the C-4 position. Most of the analogues bearing either acyclic or cyclic alkyl substituents showed inducing activity. In contrast, the phenyl substituted analogues displayed significant antagonist activity. We hypothesized that the antagonist activity of the phenyl compounds may result from the interaction between the aryl group and aromatic amino acids of the Lux R receptor, preventing it from adopting the active dimeric form. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00124-5

文献信息

• COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA
  申请人：BLACKWELL Helen E.

  公开号：US20100305182A1

  公开（公告）日：2010-12-02

  The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.

  本发明提供了调节群体感应细菌的通讯和毒力的组合物和方法。在各种示例实施方案中，本发明提供了一种群体感应化合物的组合库，包括天然存在和非天然存在的酰基-同型半乳糖内酯（AHL）类似物的合成类似物，以及这些化合物的合成和使用方法。
• Modulation of Bacterial Quorum Sensing with Synthetic Ligands
  申请人：Blackwell Helen E.

  公开号：US20080312319A1

  公开（公告）日：2008-12-18

  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：Blackwell Helen E.

  公开号：US20110212860A1

  公开（公告）日：2011-09-01

  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：US20150080349A1

  公开（公告）日：2015-03-19

  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.
• US7642285B2
  申请人：——

  公开号：US7642285B2

  公开（公告）日：2010-01-05