3-hydroxy-6-(4-methoxyphenylcarbamoyl)hexanoic acid benzyl ester | 876760-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-hydroxy-6-(4-methoxyphenylcarbamoyl)hexanoic acid benzyl ester
• CAS: 876760-87-1
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: ACHRMTQJKZACJY-UHFFFAOYSA-N

物化性质

• 沸点：
  602.6±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-6-(4-methoxyphenylcarbamoyl)hexanoic acid benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 3-hydroxyheptanedioic acid 7-[(4-methoxyphenyl)amide] 1-[(2-oxotetrahydrofuran-3-yl)amide]
  参考文献：
  名称：

  Antibody Interference with N-Acyl Homoserine Lactone-Mediated Bacterial Quorum Sensing

  摘要：

  Many bacterial pathogens coordinate their virulence factor expression in a cell density-dependent manner. This population-dependent coordination of gene expression in bacteria has been termed "quorum sensing" (QS). N-Acyl homoserine lactones (AHLs) are used by over 70 Gram-negative bacterial species as autoinducers. Inhibition of QS signaling might represent a new target for antimicrobial therapy. Here we report the hapten design, synthesis, generation of monoclonal antibodies (mAbs) against AHLs, and the evaluation of these mAbs for their ability to blunt QS signaling and inhibit virulence factor expression in P. aeruginosa. The mAbs can be envisioned as a tool for future investigations into AHL-based QS, which may aid in gaining new insights into the pathogenesis of P. aeruginosa and may ultimately lead to the development of new strategies to combat bacterial diseases.

  DOI：

  10.1021/ja0578698
• 作为产物：
  描述：

  戊二酸酐 在 sodium tetrahydroborate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.33h， 生成 3-hydroxy-6-(4-methoxyphenylcarbamoyl)hexanoic acid benzyl ester
  参考文献：
  名称：

  Antibody Interference with N-Acyl Homoserine Lactone-Mediated Bacterial Quorum Sensing

  摘要：

  Many bacterial pathogens coordinate their virulence factor expression in a cell density-dependent manner. This population-dependent coordination of gene expression in bacteria has been termed "quorum sensing" (QS). N-Acyl homoserine lactones (AHLs) are used by over 70 Gram-negative bacterial species as autoinducers. Inhibition of QS signaling might represent a new target for antimicrobial therapy. Here we report the hapten design, synthesis, generation of monoclonal antibodies (mAbs) against AHLs, and the evaluation of these mAbs for their ability to blunt QS signaling and inhibit virulence factor expression in P. aeruginosa. The mAbs can be envisioned as a tool for future investigations into AHL-based QS, which may aid in gaining new insights into the pathogenesis of P. aeruginosa and may ultimately lead to the development of new strategies to combat bacterial diseases.

  DOI：

  10.1021/ja0578698