4-Hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid (2-sulfamoyl-phenyl)-amide | 850814-36-7

• 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: 4-Hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid (2-sulfamoyl-phenyl)-amide
• CAS: 850814-36-7
• 化学式: C₂₀H₂₂N₄O₅S
• 分子量: 430.484
• InChiKey: NUGAZQWCURHNTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  144.38
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid (2-sulfamoyl-phenyl)-amide 在 氢氧化钾 作用下， 反应 12.0h， 以95%的产率得到3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: synthesis and structure–activity relationships of N-1-heteroalkyl-4-hydroxyquinolon-3-yl-benzothiadiazines

  摘要：

  N-1-Alkylamino and N-1-alkyloxy-4-hydroxyquinolon-3-yl benzothiadiazines were synthesized and evaluated as inhibitors of genotype 1 HCV polymerase. The N-1-alkyloxy derivatives were not potent inhibitors, however N-1-alkylamino derivatives displayed comparable potency to carbon analogs. Analogs with aliphatic substituents were significantly more potent than those with benzylic substituents against genotype la polymerase. The most potent inhibitors contained small alkyl or carbocyclic substituents and exhibited IC50's of 50-100 and 200-400 nM against genotype 1 b and 1 a HCV polymerase, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.071
• 作为产物：
  描述：

  1-异戊基-1H-吡啶并[2,3-d][1,3]噁嗪-2,4-二酮 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 4-Hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid (2-sulfamoyl-phenyl)-amide
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: synthesis and structure–activity relationships of N-1-heteroalkyl-4-hydroxyquinolon-3-yl-benzothiadiazines

  摘要：

  N-1-Alkylamino and N-1-alkyloxy-4-hydroxyquinolon-3-yl benzothiadiazines were synthesized and evaluated as inhibitors of genotype 1 HCV polymerase. The N-1-alkyloxy derivatives were not potent inhibitors, however N-1-alkylamino derivatives displayed comparable potency to carbon analogs. Analogs with aliphatic substituents were significantly more potent than those with benzylic substituents against genotype la polymerase. The most potent inhibitors contained small alkyl or carbocyclic substituents and exhibited IC50's of 50-100 and 200-400 nM against genotype 1 b and 1 a HCV polymerase, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.071