2-azido-N-(((2R,3S,4S,5R,6R)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acetamide | 1220984-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-N-(((2R,3S,4S,5R,6R)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acetamide
• CAS: 1220984-53-1
• 化学式: C₂₀H₃₇N₇O₁₂
• 分子量: 567.553
• InChiKey: WZKCFHORXKCJTE-XHWOANFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.82
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  334.45
• 氢给体数：
  11.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-azido-N-(((2R,3S,4S,5R,6R)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acetamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以96%的产率得到2-amino-N-[[(2R,3S,4S,5R,6R)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]acetamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Mono- and Di-N-acylated Aminoglycosides

  摘要：

  Despite issues with oto/nephrotoxicity and bacterial resistance, aminoglycosides (AGs) remain an effective and widely used class of antibacterial agents. For decades now, efforts toward the development of novel AGs with potential to overcome some of these problems have been major research focuses. 1-N-Acylation, especially gamma-amino-beta-hydroxybutyrate (AHB) derivatization, has proven to be one of the most successful strategies for improving the overall properties of AGs, including their ability to avoid certain resistance mechanisms. More recently, 6'-N-acylation arose as another possible strategy to improve the properties of these drugs. In this study, we report on the glycinyl, carboxybenzyl, and AHB mono- and diderivatization at the 1-, 6'-, and/or 4'''-amines of the AGs amikacin, kanamycin A, netilmicin, sisomicin, and tobramycin. We also present the antibacterial activities and the reduced reactivity of AG-modifying enzymes (AMEs) toward these new AG derivatives, and identify the AMEs present in the bacterial strains tested.

  DOI：

  10.1021/acsmedchemlett.5b00255
• 作为产物：
  描述：

  叠氮基乙酸NHS酯 、 卡那霉素碱 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以55%的产率得到2-azido-N-(((2R,3S,4S,5R,6R)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acetamide
  参考文献：
  名称：

  Synthesis and Biological Activity of Mono- and Di-N-acylated Aminoglycosides

  摘要：

  Despite issues with oto/nephrotoxicity and bacterial resistance, aminoglycosides (AGs) remain an effective and widely used class of antibacterial agents. For decades now, efforts toward the development of novel AGs with potential to overcome some of these problems have been major research focuses. 1-N-Acylation, especially gamma-amino-beta-hydroxybutyrate (AHB) derivatization, has proven to be one of the most successful strategies for improving the overall properties of AGs, including their ability to avoid certain resistance mechanisms. More recently, 6'-N-acylation arose as another possible strategy to improve the properties of these drugs. In this study, we report on the glycinyl, carboxybenzyl, and AHB mono- and diderivatization at the 1-, 6'-, and/or 4'''-amines of the AGs amikacin, kanamycin A, netilmicin, sisomicin, and tobramycin. We also present the antibacterial activities and the reduced reactivity of AG-modifying enzymes (AMEs) toward these new AG derivatives, and identify the AMEs present in the bacterial strains tested.

  DOI：

  10.1021/acsmedchemlett.5b00255

文献信息

• [EN] ANIONIC CONJUGATES OF GLYCOSYLATED BACTERIAL METABOLITE<br/>[FR] CONJUGUÉS ANIONIQUES D'UN MÉTABOLITE BACTÉRIEN GLYCOSYLÉ
  申请人：GLYCAN BIOSCIENCES PTY LTD

  公开号：WO2010037179A1

  公开（公告）日：2010-04-08

  The invention relates to anionic conjugates of glycosylated bacterial metabolites that may be used to mimic the structure and/or activity of the anionic bioactive molecules known as glycosaminoglycans (GAGs). The invention also relates to processes for the preparation of the conjugates. Such conjugates are useful in the prophylaxis and/or treatment of disease conditions and in particular chronic disease conditions such as inflammatory (including allergic) diseases, metastatic cancers and infection by pathogenic agents including bacteria, viruses or parasites.

  该发明涉及与糖基化细菌代谢产物的阴离子结合物，可用于模拟被称为糖胺聚糖（GAGs）的阴离子生物活性分子的结构和/或活性。该发明还涉及制备这些结合物的过程。这些结合物在预防和/或治疗疾病条件方面具有用处，特别是慢性疾病条件，如炎症（包括过敏）疾病、转移性癌症和感染病原体（包括细菌、病毒或寄生虫）的情况。