N-(2-hydroxy-4-nitrophenyl)-2-phenoxyacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2-hydroxy-4-nitrophenyl)-2-phenoxyacetamide
• 化学式: C₁₄H₁₂N₂O₅
• 分子量: 288.26
• InChiKey: PZTWAHGBGTWVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-4-nitrophenyl)-2-phenoxyacetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以80%的产率得到N-(4-amino-2-hydroxyphenyl)-2-phenoxyacetamide
  参考文献：
  名称：

  Nonpeptide Inhibitors of Measles Virus Entry

  摘要：

  Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-mu M blockade of the MV, one of which (AS-48) exhibits IC50 0.6-3.0 mu M across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.

  DOI：

  10.1021/jm0602559
• 作为产物：
  描述：

  苯氧乙酰氯 、 2-氨基-5-硝基苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 N-(2-hydroxy-4-nitrophenyl)-2-phenoxyacetamide
  参考文献：
  名称：

  Nonpeptide Inhibitors of Measles Virus Entry

  摘要：

  Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-mu M blockade of the MV, one of which (AS-48) exhibits IC50 0.6-3.0 mu M across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.

  DOI：

  10.1021/jm0602559