(2R,3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-[(1R,2R,3S,4R,6S)-4,6-diazido-3-benzyloxy-2-((R)-1-oxiranylmethoxy)-cyclohexyloxy]-tetrahydro-pyran | 285994-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-[(1R,2R,3S,4R,6S)-4,6-diazido-3-benzyloxy-2-((R)-1-oxiranylmethoxy)-cyclohexyloxy]-tetrahydro-pyran
• CAS: 285994-43-6
• 化学式: C₃₆H₄₀N₁₂O₇
• 分子量: 752.79
• InChiKey: VATVIGJHGBOVTQ-QZIIBGCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  55.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  262.95
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-[(1R,2R,3S,4R,6S)-4,6-diazido-3-benzyloxy-2-((R)-1-oxiranylmethoxy)-cyclohexyloxy]-tetrahydro-pyran 在 MP-TsOH resin sodium hydroxide 、 水 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-hydroxy-2-[(2R)-2-hydroxy-3-(methylamino)propoxy]cyclohexyl]oxyoxane-3,4-diol
  参考文献：
  名称：

  靶向细菌 rRNA 并抑制耐药酶的双功能抗生素的设计

  摘要：

  DOI：

  10.1021/ja000575w
• 作为产物：
  描述：

  (R)-对甲苯磺酸缩水甘油酯 、 1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-[(1R,2R,3S,4R,6S)-4,6-diazido-3-benzyloxy-2-((R)-1-oxiranylmethoxy)-cyclohexyloxy]-tetrahydro-pyran
  参考文献：
  名称：

  Structure–activity relationships of bivalent aminoglycosides and evaluation of their microbiological activities

  摘要：

  A library of 4,5- and 4,6-linked bivalent aminoglycoside (AMG) antibiotics consisting of neamine and nebramine pharmacophores have been synthesized. We probed the effect of the linker on antibiotic activity with a series of selected synthetic analogues with varied length and substituents. A number of compounds demonstrated in vitro activity against several bacterial strains and showed activity against drug resistant strains of Pseudomonas aeruginosa. Among the compounds prepared, analogues 12a-d were novel 4,6-linked AMGs containing the nebramine pharmacophore. In addition the lead compound OPT-11 possessed an ED50 of <= 5 mg/kg in a Staphylococcus aureus ATCC 29213 mouse protection model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.029