3-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-1-(2-aminoethyl)-1-hydroxyurea | 75178-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-1-(2-aminoethyl)-1-hydroxyurea
• CAS: 75178-74-4
• 化学式: C₂₁H₄₂N₆O₁₃
• 分子量: 586.597
• InChiKey: RVLZIRGCVBUBHG-SRLYWJMCSA-N

物化性质

• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.89
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  335.18
• 氢给体数：
  13.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  3-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-1-(2-aminoethyl)-1-hydroxyurea 在 Ra-Ni 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.0h， 以70%的产率得到
  参考文献：
  名称：

  Probing the functional requirements of the l-haba side-chain of amikacin—synthesis, 16S A-site rRNA binding, and antibacterial activity

  摘要：

  The 1-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01625-3
• 作为产物：
  描述：

  3,6'-bis-N-benzyloxycarbonylkanamycin A 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 70.67h， 生成 3-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-1-(2-aminoethyl)-1-hydroxyurea
  参考文献：
  名称：

  Probing the functional requirements of the l-haba side-chain of amikacin—synthesis, 16S A-site rRNA binding, and antibacterial activity

  摘要：

  The 1-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01625-3