(2R,2'R)-3,3'-(butane-1,4-diylbis(azanediyl))bis(1-(((1R,2R,3S,5R,6S)-3,5-diazido-2-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((benzyloxy)methoxy)cyclohexyl)oxy)propan-2-ol) | 688763-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,2'R)-3,3'-(butane-1,4-diylbis(azanediyl))bis(1-(((1R,2R,3S,5R,6S)-3,5-diazido-2-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((benzyloxy)methoxy)cyclohexyl)oxy)propan-2-ol)
• CAS: 688763-89-5
• 化学式: C₆₄H₈₄N₂₆O₁₄
• 分子量: 1441.54
• InChiKey: WJDMPZUHKKONNF-AYICEOGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.23
• 重原子数：
  104.0
• 可旋转键数：
  45.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  565.36
• 氢给体数：
  4.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  (2R,2'R)-3,3'-(butane-1,4-diylbis(azanediyl))bis(1-(((1R,2R,3S,5R,6S)-3,5-diazido-2-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((benzyloxy)methoxy)cyclohexyl)oxy)propan-2-ol) 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 生成
  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
• 作为产物：
  描述：

  四亚甲基二胺 、 5-O-[(2R)-glycidyl]-6-O-benzyloxymethoxy-4'-O-benzyl perazidonebramine 以 乙醇 为溶剂， 反应 48.0h， 生成 (2R,2'R)-3,3'-(butane-1,4-diylbis(azanediyl))bis(1-(((1R,2R,3S,5R,6S)-3,5-diazido-2-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((benzyloxy)methoxy)cyclohexyl)oxy)propan-2-ol)
  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

文献信息

• Dimeric Aminoglycosides as Antibiotics
  作者：Fabio Agnelli、Steven J. Sucheck、Kenneth A. Marby、David Rabuka、Su-Lan Yao、Pamela S. Sears、Fu-Sen Liang、Chi-Huey Wong

  DOI：10.1002/anie.200353225

  日期：2004.3.12