hexa N-phenylacetyl-neomycin B | 1428669-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexa N-phenylacetyl-neomycin B
• 英文别名: N-[[(2R,3S,4R,5R,6R)-6-[(1R,2R,3S,4R,6S)-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-4,5-dihydroxy-3-[(2-phenylacetyl)amino]-6-[[(2-phenylacetyl)amino]methyl]oxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-4,6-bis[(2-phenylacetyl)amino]cyclohexyl]oxy-3,4-dihydroxy-5-[(2-phenylacetyl)amino]oxan-2-yl]methyl]-2-phenylacetamide
• CAS: 1428669-52-6
• 化学式: C₇₁H₈₂N₆O₁₉
• 分子量: 1323.46
• InChiKey: LUTJLUFSHGFXHL-VTTGZKGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  96
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  372
• 氢给体数：
  13
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  新霉素标液 、 phenylacetic acid N-hydroxysuccinimide ester 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以24%的产率得到hexa N-phenylacetyl-neomycin B
  参考文献：
  名称：

  Selective Inhibition of Bacterial and Human Topoisomerases by N-Arylacyl O-Sulfonated Aminoglycoside Derivatives

  摘要：

  Numerous therapeutic applications have been proposed for molecules that bind heparin-binding proteins. Development of such compounds has primarily focused on optimizing the degree and orientation of anionic groups on a scaffold, but utility of these polyanions has been diminished by their typically large size and nonspecific interactions with many proteins. In this study, N-arylacyl O-sulfonated aminoglycosides were synthesized and evaluated for their ability to selectively inhibit structurally similar bacterial and human topoisomerases. It is demonstrated that the structure of the aminoglycoside and of the N-arylacyl moiety imparts selective inhibition of different topoisomerases and alters the mechanism. The results here outline a strategy that will be applicable to identifying small, structurally defined oligosaccharides that bind heparin-binding proteins with a high degree of selectivity.

  DOI：

  10.1021/ml3004507