N¹-<(S)-γ-amino-α-hydroxybutyryl>nebramine | 82472-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N¹-<(S)-γ-amino-α-hydroxybutyryl>nebramine
• 英文别名: (2S)-4-amino-N-[(2R,3R,5S,6R)-6-(aminomethyl)-2-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-5-hydroxyoxan-3-yl]-2-hydroxybutanamide
• CAS: 82472-95-5
• 化学式: C₁₆H₃₃N₅O₇
• 分子量: 407.467
• InChiKey: HQLXUZKSCHNUNQ-HGOJFKKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.22
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  232.56
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N^6'-(benzyloxycarbonyl)-N^2'-<(S)-γ-<(benzyloxycarbonyl)amino>-α-hydroxybutyryl>nebramine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 以70%的产率得到N¹-<(S)-γ-amino-α-hydroxybutyryl>nebramine
  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

• KIRST, H. A.;TRUEDELL, B. A.
  作者：KIRST, H. A.、TRUEDELL, B. A.

  DOI：——

  日期：——