(S)-2-(nonylthio)-N-(2-oxotetrahydrofuran-3-yl)acetamide | 252726-06-0

• 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-(nonylthio)-N-(2-oxotetrahydrofuran-3-yl)acetamide
• 英文别名: N-(nonylsulfanylacetyl)-L-homoserine lactone；2-nonylsulfanyl-N-[(3S)-2-oxooxolan-3-yl]acetamide
• CAS: 252726-06-0
• 化学式: C₁₅H₂₇NO₃S
• 分子量: 301.45
• InChiKey: BBFNPHOSVOHFJR-ZDUSSCGKSA-N

物化性质

• 沸点：
  510.1±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(nonylthio)-N-(2-oxotetrahydrofuran-3-yl)acetamide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以36%的产率得到2-(nonylsulfinyl)-N-((S)-2-oxotetrahydrofuran-3-yl)acetamide
  参考文献：
  名称：

  Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic

  摘要：

  报道了一种通过一锅法或连续方法实现的并行解决相合成硫化物AHL类似物（10a–s）。相应的亚砜13a–e和亚磺酸14a–e被制备，以扩展19个成员的硫化物阵列10a–s的多样性。同样，二硫烷12a–c的制备在结构上既与硫化物10a–s相似，也与大蒜中的生物活性结构相似。本研究中所有化合物的设计和生物筛选旨在抑制群体感应，其中包括对转录调节因子LuxR和LasR的竞争性抑制。设计基于从大蒜中分离出的分子组分中的结合位点和结构特征内的关键相互作用，这些组分7和8已被证明是群体感应抑制剂，但不是抗生素。识别出一种有效的群体感应抑制剂N-(庚基硫酰乙酰)-L-同型半胱氨酸内酯（10c）。结合对其他类似物收集的数据，结果的结构-活性关系提出了一个假设，即假定存在竞争性结合。

  DOI：

  10.1039/b415761c
• 作为产物：
  描述：

  1-辛硫醇 在 三乙胺 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 (S)-2-(nonylthio)-N-(2-oxotetrahydrofuran-3-yl)acetamide
  参考文献：
  名称：

  Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

  摘要：

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

  DOI：

  10.1021/jm2001019

文献信息

• Autoinducer compounds
  申请人：The Research & Development Institute, Inc.

  公开号：US06337347B1

  公开（公告）日：2002-01-08

  Autoinducer compounds which enhance gene expression in a wide variety of microorganisms, therapeutic compositions and therapeutic methods wherein gene expression within microorganisms is regulated are disclosed.

  自动诱导化合物可以增强各种微生物的基因表达，公开了基因表达在微生物内部受到调控的治疗组合物和治疗方法。
• Methods and compositions for controlling biofilm development
  申请人：Davies G. David

  公开号：US20070110680A1

  公开（公告）日：2007-05-17

  A method of cleaning or protecting surfaces by treatment with compositions comprising N-(3-oxododecanoyl)-L-homoserine lactone (OdDHL) blocking compounds and/or N-butyryl-L-homoserine lactone (BHL) analogs, either in combination or separately.
• Antimicrobial dental materials, restorations, and prostheses
  申请人：Jernberg R. Gary

  公开号：US20070172434A1

  公开（公告）日：2007-07-26

  The present invention relates to compositions and methods for antimicrobial dental materials in the restoration of the sequelae of oral infections including replacement of oral tissues lost to disease and prevention of additional infections.