| 1437593-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1437593-56-0
• 化学式: C₆₄H₁₁₇N₅O₂₃S
• 分子量: 1356.72
• InChiKey: HDLOXQUAZKIXBX-MFAWZYSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  93.0
• 可旋转键数：
  30.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  388.64
• 氢给体数：
  12.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  在 三氟乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.05h， 以100%的产率得到(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6S)-3-amino-6-(hexadecylsulfanylmethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol
  参考文献：
  名称：

  Di-alkylated paromomycin derivatives: Targeting the membranes of Gram positive pathogens that cause skin infections

  摘要：

  A collection of paromomycin-based di-alkylated cationic amphiphiles differing in the lengths of their aliphatic chain residues were designed, synthesized, and evaluated against 14 Gram positive pathogens that are known to cause skin infections. Paromomycin derivatives that were di-alkylated with C-7 and C-8 linear aliphatic chains had improved antimicrobial activities relative to the parent aminoglycoside as well as to the clinically used membrane-targeting antibiotic gramicidin D; several novel derivatives were at least 16-fold more potent than the parent aminoglycoside paromomycin. Comparison between a di-alkylated and a mono-alkylated paromomycin indicated that the di-alkylation strategy leads to both an improvement in antimicrobial activity and to a dramatic reduction in undesired red blood cell hemolysis caused by many aminoglycoside-based cationic amphiphiles. Scanning electron microscopy provided evidence for cell surface damage by the reported di-alkylated paromomycins. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.046
• 作为产物：
  描述：

  在 吡啶 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  [EN] MEMBRANE-TARGETING AMINOGLYCOSIDE-BASED CATIONIC AMPHIPHILES AND THERAPEUTIC USES
  [FR] AMPHIPHILES CATIONIQUES À BASE D'AMINOGLYCOSIDE, CIBLANT LES MEMBRANES, ET UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本发明涉及两性的氨基糖苷（AG）衍生物，特别是托布拉霉素、卡那霉素A和帕罗莫霉素的衍生物，这些衍生物包括通过各种连接剂连接到AG基团的疏水侧链。这些新颖的衍生物可用作靶向细菌细胞膜的广谱抗菌剂，同时由于对真核细胞膜的非选择性靶向作用，具有最小毒性。本发明还涉及制备这些新颖衍生物的方法、包括这些化合物的药物组合物、以及使用这些化合物和组合物的方法，特别是作为靶向细菌细胞膜的抗菌剂，用于治疗细菌感染和抑制生物膜生长。

  公开号：

  WO2014013495A1