acetaldehyde O-(5-hydroxy-2-nitrobenzyl) oxime | 1290543-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: acetaldehyde O-(5-hydroxy-2-nitrobenzyl) oxime
• CAS: 1290543-31-5
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: OUPTYEVFHZRXER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.96
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  acetaldehyde O-(5-hydroxy-2-nitrobenzyl) oxime 在 四氯化碳 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-(((ethylideneamino)oxy)methyl)-4-nitrophenyl dihydrogen phosphate
  参考文献：
  名称：

  Utilization of Nitrophenylphosphates and Oxime-Based Ligation for the Development of Nanomolar Affinity Inhibitors of the Yersinia pestis Outer Protein H (YopH) Phosphatase

  摘要：

  Our current study reports the first K(M) optimization of a library of nitrophenylphosphate-containing substrates for generating an inhibitor lead against the Yersinia pestis outer protein phosphatase (YopH). A high activity substrate identified by this method (K(M) = 80 mu M) was converted from a subs trate into an inhibitor by replacement of its phosphate group with difluoromethylphosphonic acid, and by attachment of an aminooxy handle for further structural optimization by mime ligation. A cocrystal structure of this aminooxy-containing platform in complex with YopH allowed the identification of a conserved water molecule proximal to the aminooxy group that was subsequenly employed for the design of furanyl-based oxime derivatives. By this process, a potent (IC(50) = 190 nM) and nonpromiscuous inhibitor was developed with good YopH selectivity relative to a panel of phosphatases. The inhibitor showed significant inhibition Of intracellular Y pestis replication at a noncytotoxic concentration. The current work presents general approaches to PTP inhibitor development that may be useful beyond YopH.

  DOI：

  10.1021/jm200022g