1L-O⁴-(3-amino-N,O²-carbonyl-α-D-3-deoxy-glucopyranosyl)-O⁶-(6-amino-N,O⁴-carbonyl-α-D-6-deoxy-glucopyranosyl)-2-deoxy-streptamine | 69783-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1L-O⁴-(3-amino-N,O²-carbonyl-α-D-3-deoxy-glucopyranosyl)-O⁶-(6-amino-N,O⁴-carbonyl-α-D-6-deoxy-glucopyranosyl)-2-deoxy-streptamine
• 英文别名: (4aR,6R,7R,8R,8aS)-6-[(1R,2S,3S,4R,6S)-3-[[(3aR,4S,6R,7S,7aS)-7-hydroxy-6-(hydroxymethyl)-2-oxo-1,3a,4,6,7,7a-hexahydropyrano[4,3-d][1,3]oxazol-4-yl]oxy]-4,6-diamino-2-hydroxycyclohexyl]oxy-7,8-dihydroxy-4,4a,6,7,8,8a-hexahydro-3H-pyrano[2,3-e][1,3]oxazin-2-one
• CAS: 69783-65-9
• 化学式: C₂₀H₃₂N₄O₁₃
• 分子量: 536.493
• InChiKey: PCYZTGDESDMBLC-JXLUWRRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  267
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1,3,6',2''-tetra-N-benzyloxycarbonyl-kanamycin A 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 1L-O⁴-(3-amino-N,O²-carbonyl-α-D-3-deoxy-glucopyranosyl)-O⁶-(6-amino-N,O⁴-carbonyl-α-D-6-deoxy-glucopyranosyl)-2-deoxy-streptamine
  参考文献：
  名称：

  Aminoglycoside antibiotics. 2. N, N-Dialkylkanamycins

  摘要：

  N6',N3''-Dialkyl derivatives of kanamycins A and B were prepared regiospecifically from the parent antibiotics. Although the dimethyl and diethyl derivatives of kanamycin A were inactive in standard antibacterial assays, the dimethyl derivative of kanamycin B showed moderate activity, especially against various strains of Pseudomonas aeruginosa. A method for the selective dimethylation of the 3''-amino group of kanamycin A also was developed.

  DOI：

  10.1021/jm00190a015

文献信息

• Aminoglycoside antibiotics. 2. N, N-Dialkylkanamycins
  作者：Virendra Kumar、William A. Remers

  DOI：10.1021/jm00190a015

  日期：1979.4

  N6',N3''-Dialkyl derivatives of kanamycins A and B were prepared regiospecifically from the parent antibiotics. Although the dimethyl and diethyl derivatives of kanamycin A were inactive in standard antibacterial assays, the dimethyl derivative of kanamycin B showed moderate activity, especially against various strains of Pseudomonas aeruginosa. A method for the selective dimethylation of the 3''-amino group of kanamycin A also was developed.