4-amino-N-((5aR,6R,7S,8R,9aS)-6,7-dihydroxy-5a,6, 7,8,9,9ahexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl)butanamide | 1554421-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-amino-N-((5aR,6R,7S,8R,9aS)-6,7-dihydroxy-5a,6, 7,8,9,9ahexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl)butanamide
• CAS: 1554421-69-0
• 化学式: C₁₃H₂₁N₅O₄
• 分子量: 311.341
• InChiKey: KWDDWMCNHYYNOY-FWEIOOQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  135.52
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  tert-butyl (4-(((3a'S,3b'R,9a'S,11'R,11a'S)-3a',3b',9a',10',11',11a'-hexahydro-5'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4',5':5,6]benzo[1,2-b][1,2,3]triazolo[1,5-d][1,4]oxazin]-11'-yl)amino)-4-oxobutyl)carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以79%的产率得到4-amino-N-((5aR,6R,7S,8R,9aS)-6,7-dihydroxy-5a,6, 7,8,9,9ahexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl)butanamide
  参考文献：
  名称：

  Synthesis of triazole-functionalized 2-DOS analogues and their evaluation as A-site binders

  摘要：

  Aminoglycoside-antibiotics represent important tools for studying the biological functions of RNA. An orthogonal protection strategy applied on 2-deoxystreptamine (2-DOS) revealed a series of key intermediates that enable its regioselective functionalization. Our approach allowed the construction of selected representatives of triazole-containing analogues with diverse molecular frameworks for biological evaluation regarding their binding and antibacterial potencies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.125