ETH 100 | 82472-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ETH 100
• 英文别名: N^2'-<(S)-γ-amino-α-hydroxybutyryl>apramycin；2'-N-[(2S)-4-amino-2-hydroxybutyryl]apramycin tetraacetate；2'-N-[4-amino-2(S)-hydroxybutyryl]apramycin；N^2'-((S)-γ-amino-α-hydroxybutyryl)apramycin
• CAS: 82472-91-1
• 化学式: C₂₅H₄₈N₆O₁₃
• 分子量: 640.689
• InChiKey: RISJNZRYYPANNC-HRSWKRDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.08
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  332.97
• 氢给体数：
  13.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  安普霉素 在 20% palladium hydroxide-activated charcoal 、 氢气 、 nickel(II) acetate tetrahydrate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 26.0 ℃ 、101.33 kPa 条件下， 反应 31.0h， 生成 ETH 100
  参考文献：
  名称：

  TREATMENT OF BACTERIAL INFECTIOUS DISEASES

  摘要：

  本发明涉及一种新型的药理治疗人类细菌感染疾病的方法。具体而言，该发明涉及使用式（I）的阿帕霉素或阿帕霉素衍生物来治疗人类细菌感染疾病。实验证明，阿帕霉素出人意料地并没有观察到与相关氨基糖苷类抗生素相似的高毒性水平，而实际上甚至比已在人类医学中使用的庆大霉素等化合物毒性显著更低。

  公开号：

  US20130165397A1

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.
• TREATMENT OF BACTERIAL INFECTIOUS DISEASES
  申请人：Boettger Erik

  公开号：US20130165397A1

  公开（公告）日：2013-06-27

  The present invention relates to a novel pharmacological treatment of bacterial infectious diseases in humans. Specifically the invention relates to the use of apramycin of formula (I) or apramycin derivatives to treat bacterial infectious diseases in humans. It is demonstrated that apramycin surprisingly does not have the expected high level of toxicity observed with related aminoglycoside antibiotics but actually is even significantly less toxic than compounds already used in human medicine such as gentamicin.

  本发明涉及一种新型的药理治疗人类细菌感染疾病的方法。具体而言，该发明涉及使用式（I）的阿帕霉素或阿帕霉素衍生物来治疗人类细菌感染疾病。实验证明，阿帕霉素出人意料地并没有观察到与相关氨基糖苷类抗生素相似的高毒性水平，而实际上甚至比已在人类医学中使用的庆大霉素等化合物毒性显著更低。