N-[(E)-3-oxo-6-dodecenoyl]-L-homoserine lactone | 429675-30-9

• 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-[(E)-3-oxo-6-dodecenoyl]-L-homoserine lactone
• 英文别名: (E)-3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodec-6-enamide
• CAS: 429675-30-9
• 化学式: C₁₆H₂₅NO₄
• 分子量: 295.379
• InChiKey: MJZVDDVMMUIMCG-UZYOAWRESA-N

物化性质

• 沸点：
  531.2±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  反式-4-癸烯酸乙酯 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 72.0h， 生成 N-[(E)-3-oxo-6-dodecenoyl]-L-homoserine lactone
  参考文献：
  名称：

  Targeting Staphylococcus aureus Quorum Sensing with Nonpeptidic Small Molecule Inhibitors

  摘要：

  A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.

  DOI：

  10.1021/jm500215s

文献信息

• Methods of treating or preventing an infectious disease using an immunogenic conjugate of a gram-negative bacterial autoinducer molecule or antibodies that immunospecifically bind a gram-negative bacterial autoinducer molecule
  申请人：Kende S. Andrew

  公开号：US20070231839A1

  公开（公告）日：2007-10-04

  The present invention relates to an immunogenic conjugate comprising a carrier molecule coupled to an autoinducer of a Gram negative bacteria The immunogenic conjugate, when combined with a pharmaceutically acceptable carrier, forms a suitable vaccine for mammals to prevent infection by the Gram negative bacteria The immunogenic conjugate is also used to raise and subsequently isolate antibodies or binding portions thereof which are capable of recognizing and binding to the autoinducer. The antibodies or binding portions thereof are utilized in a method of treating infections, a method of inhibiting autoinducer activity, and in diagnostic assays which detect the presence of autoinducers or autoinducer antagonists in fluid or tissue samples. TABLE OF CONTENTS Page 1. FIELD OF THE INVENTION 1 2. BACKGROUND OF THE INVENTION 1 3. SUMMARY OF THE INVENTION 4 4. BRIEF DESCRIPTION OF THE DRAWINGS 7 5. DETAILED DESCRIPTION OF THE INVENTION 7 5.1 Isolation and Synthesis of Homoserine Lactones 7 5.2 Bacterial Autoinducer Conjugation to a Carrier 17 5.3 Generation of Antibodies to BAI Immunogenic conjugates 19 5.4 Therapeutic Uses of Immunogenic conjugates 22 or Antibodies Thereto 5.4.1 Administration and Formulation 22 5.4.2 Effective Dose 25 5.5 Diagnostic Methods 27 6. EXAMPLE: SYNTHESIS 32 Preparation of Compound C 32 Preparation of Compound D 32 Preparation of Compound 5 32 Preparation of Compound 6 33 Preparation of Compound 7 33 Preparation of Compound 8 33 Preparation of Compound 10 34 Preparation of Compound 11 34 Preparation of Compound 13 35 Preparation of Compound 12 35 Preparation of Compound 14 35 Preparation of Compound 15 36 Preparation of Compound 17 36 Preparation of Compound 21 37 Preparation of Compound 22 37 Preparation of Compound 24 38 Preparation of Compound 25 38 Preparation of Compound 27 38 Preparation of Compound 29 39 7. EXAMPLE: PRODUCTION OF BAI ANTIBODIES 39 7.1 PAI'S Role In Virulence 39 7.2 Anti-PAI Polyclonal Antibodies 40 7.3 Neutralization of PAI With Antibodies 40
• US7384639B2
  申请人：——

  公开号：US7384639B2

  公开（公告）日：2008-06-10
• Targeting <i>Staphylococcus aureus</i> Quorum Sensing with Nonpeptidic Small Molecule Inhibitors
  作者：Ewan J. Murray、Rebecca C. Crowley、Alex Truman、Simon R. Clarke、James A. Cottam、Gopal P. Jadhav、Victoria R. Steele、Paul O’Shea、Catharina Lindholm、Alan Cockayne、Siri Ram Chhabra、Weng C. Chan、Paul Williams

  DOI：10.1021/jm500215s

  日期：2014.3.27

  A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.