N-valeryl-DL-homoserine lactone | 18725-17-2

• 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-valeryl-DL-homoserine lactone
• 英文别名: N-Valeryl-DL-homoserin-lacton；N-(2-oxooxolan-3-yl)pentanamide
• CAS: 18725-17-2；99063-14-6；148497-11-4
• 化学式: C₉H₁₅NO₃
• mdl: MFCD24393431
• 分子量: 185.223
• InChiKey: BFIMURGDHGARTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-valeryl-DL-homoserine lactone 在 sodium azide 、 三氟甲磺酸酐 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以68%的产率得到3-(5-n-butyl-1H-tetrazol-1-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

  摘要：

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.007
• 作为产物：
  描述：

  α-氨基-γ-丁内酯氢溴酸盐 在 sodium carbonate 作用下， 生成 N-valeryl-DL-homoserine lactone
  参考文献：
  名称：

  Sudo, Nippon Kagaku Zasshi, 1958, vol. 79, p. 81,83

  摘要：

  DOI：

文献信息

• New derivatives of alpha-amino-gamma-butyrolactone, method for the preparation thereof and pharmaceutical compositions containing them
  申请人：Laboratorio Farmaceutico C.T. s.r.l.

  公开号：EP0151964A2

  公开（公告）日：1985-08-21

  The present invention relates to new derivatives of α-amino-γ-butyrolactone and their pharmaceutically acceptable salts, endowed with anti-convulsant, anti-epileptic, sedative action and able to inhibit the ingestion of alcohol and intoxicating drinks. The invention relates also to the method for preparing the derivatives of the invention as well as the pharmaceutical compositions containing them.

  本发明涉及α-氨基-γ-丁内酯的新衍生物及其药学上可接受的盐类，具有抗惊厥、抗癫痫和镇静作用，并能抑制酒精和醉酒饮料的摄入。 本发明还涉及本发明衍生物的制备方法以及含有这些衍生物的药物组合物。
• Methods for the treatment of an infectious bacterial disease with anti-lactone or lactone derived signal molecules antibody
  申请人：Haptogen Ltd

  公开号：EP2260868A2

  公开（公告）日：2010-12-15

  The present invention relates to methods for the control of virulence of infectious bacteria by modulating the extra-cellular concentration of bacterial cell signalling molecules. Derivatives of cell signalling molecules are conjugated to suitable carrier proteins and used to isolate high affinity receptors recognising the native signal molecule(s). By binding to signalling molecules, the receptors reduce and maintain extra-cellular concentrations of signal molecules below the threshold level that would otherwise result in certain opportunistic pathogens adopting a virulent form, and can transform virulent organisms to non-virulent states. These receptors have applications for the treatment of individuals with susceptibility to infection, the treatment of patients with existing infections, in disease monitoring and management, and in related applications where the host for infection is an animal or plant.

  本发明涉及通过调节细菌细胞信号分子的细胞外浓度来控制传染性细菌毒力的方法。细胞信号分子的衍生物与适当的载体蛋白连接，并用于分离识别原生信号分子的高亲和力受体。通过与信号分子结合，受体可将信号分子的细胞外浓度降低并维持在阈值水平以下，否则会导致某些机会性病原体采取毒性形式，并可将毒性生物转化为非毒性状态。这些受体可用于治疗易受感染者、治疗现有感染患者、疾病监测和管理，以及感染宿主为动物或植物的相关应用。
• Methods for inducing autolysis in infectious bacteria
  申请人：Haptogen Ltd

  公开号：EP2261260A2

  公开（公告）日：2010-12-15

  The present invention relates to methods for the killing of infectious bacteria by modulating the extra-cellular concentration of bacterial cell signalling molecules. This has the effect of inducing rapid cell death (autolysis) in the majority of bacterial cells, and preventing virulence or restoring a benign state in surviving cells. These receptors have applications for the treatment of individuals with susceptibility to infection, the treatment of patients with existing infections, in disease management, and in related applications where the host for infection is an animal or plant. The compositions described herein are particularly relevant to Pseudomonas aeruginosa infection, for example in the treatment of pulmonary infection in cystic fibrosis patients, and represent a unique bactericidal medication that does not directly target the bacteria.

  本发明涉及通过调节细菌细胞信号分子的细胞外浓度来杀死传染性细菌的方法。其效果是诱导大多数细菌细胞快速死亡（自溶），防止毒力增强或使存活细胞恢复良性状态。这些受体可用于治疗易受感染的个体、治疗已有感染的病人、疾病管理以及感染宿主为动物或植物的相关应用。本文所述组合物尤其适用于铜绿假单胞菌感染，例如用于治疗囊性纤维化患者的肺部感染，是一种不直接针对细菌的独特杀菌药物。
• METHODS FOR THE TREATMENT OF AN INFECTIOUS BACTERIAL DISEASE WITH AN ANTI-LACTONE OR LACTONE DERIVED SIGNAL MOLECULES ANTIBODY
  申请人：Haptogen Ltd

  公开号：EP1528935B1

  公开（公告）日：2012-03-21
• Methods For Inducing Autolysis In Infectious Bacteria
  申请人：Charlton Alan Keith

  公开号：US20070218058A1

  公开（公告）日：2007-09-20

  The present invention relates to methods for the killing of infectious bacteria by modulating the extra-cellular concentration of bacterial cell signalling molecules. This has the effect of inducing rapid cell death (autolysis) in the majority of bacter cells, and preventing virulence or restoring a benign state in surviving cells. These receptors have applications for the treatment of individuals with susceptibility to infection, the treatment of patients with existing infections, in disease management, and in related applications where the host for infection is an animal or plant. The compositions described herein are particularly relevant to Pseudomonas aeruginosa infection, for example in the treatment of pulmonary infection in cystic fibrosis patients, and represent a unique bactericidal medication that does not directly target the bacteria.