methyl 6-(4-nitrophenylsulfonylamido)-6-deoxy-α-D-mannopyranoside | 1446093-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-(4-nitrophenylsulfonylamido)-6-deoxy-α-D-mannopyranoside
• 英文别名: 4-nitro-N-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]benzenesulfonamide
• CAS: 1446093-49-7
• 化学式: C₁₃H₁₈N₂O₉S
• 分子量: 378.36
• InChiKey: XMBJCYIDIWGUNQ-BNDIWNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  180
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 6-azido-6-deoxy-α-D-mannopyranoside 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 6-(4-nitrophenylsulfonylamido)-6-deoxy-α-D-mannopyranoside
  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

文献信息

• [EN] GLYCOMIMETICS AS PSEUDOMONAS AERUGINOSA LECTIN INHIBITORS<br/>[FR] GLYCOMIMÉTIQUES À TITRE D'INHIBITEURS DE LECTINE DE PSEUDOMONAS AERUGINOSA
  申请人：UNIV KONSTANZ

  公开号：WO2013152848A1

  公开（公告）日：2013-10-17

  The present invention relates to fucose- and mannose-derived glycomimetics and their general use in prophylaxis or treatment of Pseudomonas aeruginosa infections including respiratory tract infections, urinary tract infections, nosocomial infections and chronic wound infections in a patient encompassing a patient suffering already from cystic fibrosis. Said glycomimetics are inhibitors of Pseudomonas aeruginosa lectin LecB.

  本发明涉及与藻糖和甘露糖衍生的糖类类似物及其在预防或治疗包括呼吸道感染、尿道感染、医院感染和慢性伤口感染在内的假单胞菌感染中的一般用途，涉及患有囊性纤维化的患者。所述的糖类类似物是假单胞菌凝集素LecB的抑制剂。
• Glycomimetics as pseudomonas Aeruginosa lectin inhibitors
  申请人：Universität Konstanz

  公开号：EP2650289B1

  公开（公告）日：2016-07-27
• Glycomimetics As Pseudomonas Aeruginosa Lectin Inhibitors
  申请人：Universität Konstanz

  公开号：US20150361122A1

  公开（公告）日：2015-12-17

  The present invention relates to fucose- and mannose-derived glycomimetics and their general use in prophylaxis or treatment of Pseudomonas aeruginosa infections including respiratory tract infections, urinary tract infections, nosocomial infections and chronic wound infections in a patient encompassing a patient suffering already from cystic fibrosis. Said glycomimetics are inhibitors of Pseudomonas aeruginosa lectin LecB.
• US9371351B2
  申请人：——

  公开号：US9371351B2

  公开（公告）日：2016-06-21
• Discovery of Two Classes of Potent Glycomimetic Inhibitors of <i>Pseudomonas aeruginosa</i> LecB with Distinct Binding Modes
  作者：Dirk Hauck、Ines Joachim、Benjamin Frommeyer、Annabelle Varrot、Bodo Philipp、Heiko M. Möller、Anne Imberty、Thomas E. Exner、Alexander Titz

  DOI：10.1021/cb400371r

  日期：2013.8.16

  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.