methyl 5-amino-5-deoxy-D-arabinofuranoside | 243131-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-amino-5-deoxy-D-arabinofuranoside
• 英文别名: (2R,3S,4S)-2-(Aminomethyl)-5-methoxytetrahydrofuran-3,4-diol；(2R,3S,4S)-2-(aminomethyl)-5-methoxyoxolane-3,4-diol
• CAS: 243131-83-1
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: ODOKPZPCULYXKR-VRPWFDPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-amino-5-deoxy-D-arabinofuranoside 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl 5-deoxy-5-{[1-(hydroxymethyl)propyl]amino}-D-arabinofuranoside
  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：

  methyl 5-azido-5-deoxy-D-arabino-pentofuranoside 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以32%的产率得到methyl 5-amino-5-deoxy-D-arabinofuranoside
  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

文献信息

• Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Jerry D. Rose、Joseph A. Maddry、Robert N. Comber、William J. Suling、Larry N. Wilson、Robert C. Reynolds

  DOI：10.1016/s0008-6215(01)00288-9

  日期：2002.2

  Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6'-dideoxytrehalose, including N,N'-dialkylamino and 6,6'-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Ra and a panel of clinical isolates of Mycobacterium avium, 6,6'-Diamitiotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. (C) 2002 Elsevier Science Ltd. All rights reserved.