N1-glycylapramycin | 82473-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N1-glycylapramycin
• 英文别名: N¹-glycylapramycin；1-N-glycylapramycin
• CAS: 82473-03-8
• 化学式: C₂₃H₄₄N₆O₁₂
• 分子量: 596.635
• InChiKey: XBRCGQCLBZLKNA-ZSHGUCNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.83
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  312.74
• 氢给体数：
  12.0
• 氢受体数：
  17.0

反应信息

• 作为产物：
  描述：

  安普霉素 在 palladium on activated charcoal 盐酸 、 zinc diacetate 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 生成 N1-glycylapramycin
  参考文献：
  名称：

  Comparison of aminoglycoside antibiotics with respect to uptake and lethal activity in Escherichia coli

  摘要：

  Forty-five aminoglycoside antibiotics and related compounds were compared for their ability to induce the accumulation of dihydrostreptomycin in Escherichia coli K12. The common aminoglycosides and a streptothricin antibiotic all induced enhanced uptake within a relatively narrow concentration range. These concentrations were lethal to the bacteria. Comparison of aminoacyl derivatives of tobramycin and apramycin, the latter synthesized utilizing transition-metal cations to selectively control the site of substitution, revealed that 1-N-aminoacyl modifications resulted in an increased ability to induce enhanced uptake. 2'-N-Aminoacyl modifications were also effective at inducing enhanced uptake, albeit without noticeable improvement over parent. The findings from this structure-activity comparison support the proposition that aminoglycosides share a common critical target (most likely the ribosome), which, when acted upon, results in both drug accumulation and killing.

  DOI：

  10.1021/jm00385a015

文献信息

• Comparison of aminoglycoside antibiotics with respect to uptake and lethal activity in Escherichia coli
  作者：Norris E. Allen、William E. Alborn、Herbert A. Kirst、John E. Toth

  DOI：10.1021/jm00385a015

  日期：1987.2

  Forty-five aminoglycoside antibiotics and related compounds were compared for their ability to induce the accumulation of dihydrostreptomycin in Escherichia coli K12. The common aminoglycosides and a streptothricin antibiotic all induced enhanced uptake within a relatively narrow concentration range. These concentrations were lethal to the bacteria. Comparison of aminoacyl derivatives of tobramycin and apramycin, the latter synthesized utilizing transition-metal cations to selectively control the site of substitution, revealed that 1-N-aminoacyl modifications resulted in an increased ability to induce enhanced uptake. 2'-N-Aminoacyl modifications were also effective at inducing enhanced uptake, albeit without noticeable improvement over parent. The findings from this structure-activity comparison support the proposition that aminoglycosides share a common critical target (most likely the ribosome), which, when acted upon, results in both drug accumulation and killing.