methyl 4,5-dimethoxy-2-(3-phenoxybenzamido)benzoate | 878927-50-5

• 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: methyl 4,5-dimethoxy-2-(3-phenoxybenzamido)benzoate
• 英文别名: Methyl 4,5-dimethoxy-2-[(3-phenoxybenzoyl)amino]benzoate
• CAS: 878927-50-5
• 化学式: C₂₃H₂₁NO₆
• 分子量: 407.423
• InChiKey: HELDEABYNHLTGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4,5-dimethoxy-2-(3-phenoxybenzamido)benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以98%的产率得到4,5-dimethoxy-2-(3-phenoxybenzamido)benzoic acid
  参考文献：
  名称：

  Discovery of Novel Bacterial RNA Polymerase Inhibitors: Pharmacophore-Based Virtual Screening and Hit Optimization

  摘要：

  The bacterial RNA polymerase (RNAP) is a validated target for broad spectrum antibiotics. However, the efficiency of drugs is reduced by resistance. To discover novel RNAP inhibitors, a pharmacophore based on the alignment of described inhibitors was used for virtual screening. In an optimization process of hit compounds, novel derivatives with improved in vitro potency were discovered. Investigations concerning the molecular mechanism of RNAP inhibition reveal that they prevent the protein-protein interaction (PPI) between sigma(70) and the RNAP core enzyme. Besides of reducing RNA formation, the inhibitors were shown to interfere with bacterial lipid biosynthesis. The compounds were active against Gram-positive pathogens and revealed significantly lower resistance frequencies rifampicin.

  DOI：

  10.1021/jm400485e
• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 methyl 4,5-dimethoxy-2-(3-phenoxybenzamido)benzoate
  参考文献：
  名称：

  Discovery of Novel Bacterial RNA Polymerase Inhibitors: Pharmacophore-Based Virtual Screening and Hit Optimization

  摘要：

  The bacterial RNA polymerase (RNAP) is a validated target for broad spectrum antibiotics. However, the efficiency of drugs is reduced by resistance. To discover novel RNAP inhibitors, a pharmacophore based on the alignment of described inhibitors was used for virtual screening. In an optimization process of hit compounds, novel derivatives with improved in vitro potency were discovered. Investigations concerning the molecular mechanism of RNAP inhibition reveal that they prevent the protein-protein interaction (PPI) between sigma(70) and the RNAP core enzyme. Besides of reducing RNA formation, the inhibitors were shown to interfere with bacterial lipid biosynthesis. The compounds were active against Gram-positive pathogens and revealed significantly lower resistance frequencies rifampicin.

  DOI：

  10.1021/jm400485e