3"-N-methyl-5-epi-arbekacin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3"-N-methyl-5-epi-arbekacin
• 英文别名: 5-epi-3"-N-methylarbekacin；(2S)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
• 化学式: C₂₃H₄₆N₆O₁₀
• 分子量: 566.652
• InChiKey: ADCYHHFBQRHGIF-GZNIEGPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  283
• 氢给体数：
  11
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3,2',6'-tri-N-t-butoxycarbonyl-4"'-N-p-methoxybenzyloxycarbonyl-arbekacin 在 palladium on activated charcoal 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 氢气 、 sodium methylate 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3"-N-methyl-5-epi-arbekacin
  参考文献：
  名称：

  Synthesis and antibacterial activity of 5-deoxy-5-episubstituted arbekacin derivatives

  摘要：

  5-Deoxy-5-episubstituted arbekacin derivatives have been designed and efficiently synthesized. The synthetic compounds showed potent antibacterial activity against both Staphylococcus aureus, including methicillin-resistant S. aureus, and Pseudomonas aeruginosa. In particular, these derivatives were superior to arbekacin against MRSA strains expressing the bifunctional aminoglycoside-modifying enzyme AAQ6')-APH(2"). The antibacterial activity of the 5-deoxy-5-episubstituted arbekacin derivatives against Pseudomonas aeruginosa was markedly influenced by the efflux system of MexXY/OprM. The 6'-N-methyl derivative of the 5-epi arbekacin was effective against Pseudomonas aeruginosa expressing the aminoglycoside-modifying enzyme AAC(6'). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.065

文献信息

• EP1710248
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and antibacterial activity of 5-deoxy-5-episubstituted arbekacin derivatives
  作者：Yukiko Hiraiwa、Takayuki Usui、Yoshihisa Akiyama、Kazunori Maebashi、Nobuto Minowa、Daishiro Ikeda

  DOI：10.1016/j.bmcl.2007.04.065

  日期：2007.7

  5-Deoxy-5-episubstituted arbekacin derivatives have been designed and efficiently synthesized. The synthetic compounds showed potent antibacterial activity against both Staphylococcus aureus, including methicillin-resistant S. aureus, and Pseudomonas aeruginosa. In particular, these derivatives were superior to arbekacin against MRSA strains expressing the bifunctional aminoglycoside-modifying enzyme AAQ6')-APH(2"). The antibacterial activity of the 5-deoxy-5-episubstituted arbekacin derivatives against Pseudomonas aeruginosa was markedly influenced by the efflux system of MexXY/OprM. The 6'-N-methyl derivative of the 5-epi arbekacin was effective against Pseudomonas aeruginosa expressing the aminoglycoside-modifying enzyme AAC(6'). (c) 2007 Elsevier Ltd. All rights reserved.