5,3'-dideoxy-5-epifluorokanamycin B | 69413-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,3'-dideoxy-5-epifluorokanamycin B
• 英文别名: (2R,3R,4S,5S,6R)-4-amino-2-[(1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-fluorocyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
• CAS: 69413-95-2
• 化学式: C₁₈H₃₆FN₅O₈
• 分子量: 469.511
• InChiKey: QWYIVHDLPOPKNO-KUOFUPHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  248
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5,3'-dideoxy-5-epifluorokanamycin B 在 zinc diacetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5,3'-dideoxy-5-epifluoro-3''-N-trifluoroacetyl-3,2',6'-tris(N-tert-butoxycarbonyl)kanamycin B trifluoroacetate
  参考文献：
  名称：

  Synthesis of 5-deoxy-5-epifluoro derivatives of arbekacin, amikacin, and 1-N-[(S)-4-amino-2-hydroxybutanoyl]tobramycin (study on structure — toxicity relationships)

  摘要：

  As part of a study on fluorination-toxicity relationships for aminoglycoside antibiotics, 5,3'-dideoxy-5-epifluorokanamycin B (10), 5,3',4'-trideoxy-5-epifluorokanamycin B (11), 1-N-[(S)-4-amino-2-hydroxybutanoyl]-5-deoxy-5-epifluorotobramycin (19), 5-deoxy-5-epifluoroarbekacin (20), and 5-deoxy-5-epifluoroamikacin (21) have been prepared. The acute toxicities of these three 5-deoxy-5-epifluoro compounds showed values almost identical or similar to those for arbekacin (ABK) and amikacin (15), making a sharp contrast with the toxicities of the corresponding 5-deoxy-5-fluoro derivatives. This fact is explained on the basis of basicity changes (retention for the 5-epifluoro derivatives and reduction for the 5-fluoro derivatives) at the H2N-3 groups of the fluorinated compounds compared to the parent compounds; this hypothesis was substantiated by the pKa values at the H3N+-1, 3 groups (determined by the shift changes depending on pD values at C-2 and C-4, 6 in their C-13 NMR spectral of 2,5-dideoxy-5-epifluorostreptamine (23) and 2,5-dideoxy-5-fluorostreptamine (24), chosen as model compounds, and 2-deoxystreptamine (DST).

  DOI：

  10.1016/0008-6215(95)00123-b
• 作为产物：
  描述：

  Boc₅-tobramycin 在 吡啶 、 sodium methylate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 5,3'-dideoxy-5-epifluorokanamycin B
  参考文献：
  名称：

  Synthesis of 5-deoxy-5-epifluoro derivatives of arbekacin, amikacin, and 1-N-[(S)-4-amino-2-hydroxybutanoyl]tobramycin (study on structure — toxicity relationships)

  摘要：

  As part of a study on fluorination-toxicity relationships for aminoglycoside antibiotics, 5,3'-dideoxy-5-epifluorokanamycin B (10), 5,3',4'-trideoxy-5-epifluorokanamycin B (11), 1-N-[(S)-4-amino-2-hydroxybutanoyl]-5-deoxy-5-epifluorotobramycin (19), 5-deoxy-5-epifluoroarbekacin (20), and 5-deoxy-5-epifluoroamikacin (21) have been prepared. The acute toxicities of these three 5-deoxy-5-epifluoro compounds showed values almost identical or similar to those for arbekacin (ABK) and amikacin (15), making a sharp contrast with the toxicities of the corresponding 5-deoxy-5-fluoro derivatives. This fact is explained on the basis of basicity changes (retention for the 5-epifluoro derivatives and reduction for the 5-fluoro derivatives) at the H2N-3 groups of the fluorinated compounds compared to the parent compounds; this hypothesis was substantiated by the pKa values at the H3N+-1, 3 groups (determined by the shift changes depending on pD values at C-2 and C-4, 6 in their C-13 NMR spectral of 2,5-dideoxy-5-epifluorostreptamine (23) and 2,5-dideoxy-5-fluorostreptamine (24), chosen as model compounds, and 2-deoxystreptamine (DST).

  DOI：

  10.1016/0008-6215(95)00123-b

文献信息

• Synthesis of 5-deoxy-5-epifluoro derivatives of arbekacin, amikacin, and 1-N-[(S)-4-amino-2-hydroxybutanoyl]tobramycin (study on structure — toxicity relationships)
  作者：Tetsuo Shitara、Eijiro Umemura、Tsutomu Tsuchiya、Tomio Matsuno

  DOI：10.1016/0008-6215(95)00123-b

  日期：1995.10

  As part of a study on fluorination-toxicity relationships for aminoglycoside antibiotics, 5,3'-dideoxy-5-epifluorokanamycin B (10), 5,3',4'-trideoxy-5-epifluorokanamycin B (11), 1-N-[(S)-4-amino-2-hydroxybutanoyl]-5-deoxy-5-epifluorotobramycin (19), 5-deoxy-5-epifluoroarbekacin (20), and 5-deoxy-5-epifluoroamikacin (21) have been prepared. The acute toxicities of these three 5-deoxy-5-epifluoro compounds showed values almost identical or similar to those for arbekacin (ABK) and amikacin (15), making a sharp contrast with the toxicities of the corresponding 5-deoxy-5-fluoro derivatives. This fact is explained on the basis of basicity changes (retention for the 5-epifluoro derivatives and reduction for the 5-fluoro derivatives) at the H2N-3 groups of the fluorinated compounds compared to the parent compounds; this hypothesis was substantiated by the pKa values at the H3N+-1, 3 groups (determined by the shift changes depending on pD values at C-2 and C-4, 6 in their C-13 NMR spectral of 2,5-dideoxy-5-epifluorostreptamine (23) and 2,5-dideoxy-5-fluorostreptamine (24), chosen as model compounds, and 2-deoxystreptamine (DST).