(2R)-N-[[(2R,3S,4R,5S)-3-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxyoxolan-2-yl]methyl]pyrrolidine-2-carboxamide | 1092548-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-N-[[(2R,3S,4R,5S)-3-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxyoxolan-2-yl]methyl]pyrrolidine-2-carboxamide
• CAS: 1092548-15-6
• 化学式: C₂₈H₅₄N₈O₁₃
• 分子量: 710.783
• InChiKey: GBEKAZLXJWYWCL-YFBUJURRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.9
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  374
• 氢给体数：
  14
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  在 Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 (2R)-N-[[(2R,3S,4R,5S)-3-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxyoxolan-2-yl]methyl]pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Surprising Alteration of Antibacterial Activity of 5′′-Modified Neomycin against Resistant Bacteria

  摘要：

  A facile synthetic protocol for the production of neomycin B derivatives with various modifications at the 5 '' position has been developed. The structural activity relationship (SAR) against aminoglycoside resistant bacteria equipped with various aminoglycoside-modifying enzymes (AMEs) was investigated. Enzymatic and molecular modeling studies reveal that the superb substrate promiscuity of AMEs allows the resistant bacteria to cope with diverse structural modifications despite the observation that several derivatives show enhanced antibacterial activity compared to the parent neomycin. Surprisingly, when testing synthetic neomycin derivatives against other human pathogens, two leads exhibit prominent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) that are known to exert a high level of resistance against clinically used aminoglycosides. These findings can be extremely useful in developing new aminoglycoside antibiotics against resistant bacteria. Our result also suggests that. new biological and antimicrobial activities can be obtained by chemical modifications of old drugs.

  DOI：

  10.1021/jm800997s