5''-N-((4-pyrenyl)-butanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin | 1067241-26-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5''-N-((4-pyrenyl)-butanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin
• 英文别名: 5"-deoxy-5"-N-((4-pyrenyl)-butanoyl)-1,3,2',6',2'",6'"-hexa-N-(tert-butoxycarbonyl)-neomycin B；tert-butyl N-[(1S,2R,3R,4S,5R)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxan-2-yl]oxy-3-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-4,5-dihydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxan-2-yl]oxy-3-hydroxy-5-[(4-pyren-1-ylbutanoylamino)methyl]oxolan-2-yl]oxy-4-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]carbamate
• CAS: 1067241-26-2
• 化学式: C₇₃H₁₀₉N₇O₂₅
• 分子量: 1484.7
• InChiKey: AKBUUUKPYWWVGW-KSNKZTOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  105
• 可旋转键数：
  32
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  436
• 氢给体数：
  13
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  5''-N-((4-pyrenyl)-butanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 0.05h， 以91%的产率得到1,3,2',6',2''',6'''-hexaammonium-5''-deoxy-5''-N-((4-pyrenyl)-butanoyl)-neomycin hexakis(trifluoroacetate)
  参考文献：
  名称：

  Design, Synthesis, and Antibacterial Activities of Neomycin−Lipid Conjugates: Polycationic Lipids with Potent Gram-Positive Activity

  摘要：

  Aminoglycoside antibiotics and cationic detergents constitute two classes of clinically important drugs and antiseptics. Their bacteriological and clinical efficacy, however, has decreased recently due to antibiotic resistance. We have synthesized aminoglycoside-lipid conjugates in which the aminoglycoside neomycin forms the cationic headgroup of a polycationic detergent. Our results show that neomycin-C-16 and neomycin-C-20 conjugates exhibit strong Gram-positive activity but reduced Gram-negative activity. The MIC of neomycin-C-16 (C-20) conjugates against methicillin-resistant Staphylococcus aureus (MRSA) is comparable to clinically used antiseptics.

  DOI：

  10.1021/jm800345u
• 作为产物：
  描述：

  hexa-N-Boc deoxy-neomycin-5’’-amine 、 1-芘丁酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以87%的产率得到5''-N-((4-pyrenyl)-butanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin
  参考文献：
  名称：

  Design, Synthesis, and Antibacterial Activities of Neomycin−Lipid Conjugates: Polycationic Lipids with Potent Gram-Positive Activity

  摘要：

  Aminoglycoside antibiotics and cationic detergents constitute two classes of clinically important drugs and antiseptics. Their bacteriological and clinical efficacy, however, has decreased recently due to antibiotic resistance. We have synthesized aminoglycoside-lipid conjugates in which the aminoglycoside neomycin forms the cationic headgroup of a polycationic detergent. Our results show that neomycin-C-16 and neomycin-C-20 conjugates exhibit strong Gram-positive activity but reduced Gram-negative activity. The MIC of neomycin-C-16 (C-20) conjugates against methicillin-resistant Staphylococcus aureus (MRSA) is comparable to clinically used antiseptics.

  DOI：

  10.1021/jm800345u