(2R,3S,4S,5S,6S)-2-((benzylamino)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol | 1446093-36-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5S,6S)-2-((benzylamino)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol
• CAS: 1446093-36-2
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: IMINXYSREMGKIC-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  91.18
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 palladium on activated charcoal 、 氢气 、 对甲苯磺酰氯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 (2R,3S,4S,5S,6S)-2-((benzylamino)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Discovery of Two Classes of Potent Glycomimetic Inhibitors of Pseudomonas aeruginosa LecB with Distinct Binding Modes

  摘要：

  The treatment of infections due to the opportunistic pathogen Pseudomonas aeruginosa is often difficult, as a consequence of bacterial biofilm formation. Such a protective environment shields the bacterium from host defense and antibiotic treatment and secures its survival. One crucial factor for maintenance of the biofilm architecture is the carbohydrate-binding lectin LecB. Here, we report the identification of potent mannose-based LecB inhibitors from a screening of four series of mannosides in a novel competitive binding assay for LecB. Cinnamide and sulfonamide derivatives are inhibitors of bacterial adhesion with up to a 20-fold increase in affinity to LecB compared to the natural ligand methyl mannoside. Because many lectins of the host require terminal saccharides (e.g., fucosides), such capped structures as reported here may offer a beneficial selectivity profile for the pathogenic lectin. Both classes of compounds show distinct binding modes at the protein, offering the advantage of a simultaneous development of two new lead structures as anti-pseudomonadal drugs with an anti-virulence mode of action.

  DOI：

  10.1021/cb400371r