5-chloro-4-nitrobenzene-1,3-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-chloro-4-nitrobenzene-1,3-diol
• 化学式: C₆H₄ClNO₄
• 分子量: 189.555
• InChiKey: PXCOJDRVPQCTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-chloro-4-nitrobenzene-1,3-diol 在 hydrazine hydrate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 2,4-dibutoxy-6-chloroaniline
  参考文献：
  名称：

  Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

  摘要：

  Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential antivirulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of subinhibitory levels of ciprofioxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111800
• 作为产物：
  描述：

  5-氯间苯二酚 在 ammonium cerium (IV) nitrate 、 乙酸酐 、 溶剂黄146 作用下， 反应 1.0h， 生成 5-chloro-4-nitrobenzene-1,3-diol
  参考文献：
  名称：

  Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

  摘要：

  Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential antivirulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of subinhibitory levels of ciprofioxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111800