6-amino-2,5-anhydro-2,5-imino-N-benzyloxycarbonyl-1,3-O-isopropylidene-D-glucitol | 243131-87-5

• 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: 6-amino-2,5-anhydro-2,5-imino-N-benzyloxycarbonyl-1,3-O-isopropylidene-D-glucitol
• CAS: 243131-87-5
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: YZHHNICLONGCFP-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  94.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-amino-2,5-anhydro-2,5-imino-N-benzyloxycarbonyl-1,3-O-isopropylidene-D-glucitol 在 palladium on activated charcoal 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 68.0h， 生成 2,5-anhydro-6-deoxy-6-{[1-(hydroxymethyl)propyl]amino}-2,5-imino-D-glucitol
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5
• 作为产物：
  描述：

  2,5-二(羟基甲基)-3,4-吡咯烷二醇 在 镍 sodium azide 、 高氯酸 、 氢气 作用下， 以 1,4-二氧六环 、 吡啶 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 64.5h， 生成 6-amino-2,5-anhydro-2,5-imino-N-benzyloxycarbonyl-1,3-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5