N-[(2S,3R,4R,5S,6R)-6-((R)-2,3-Dihydroxy-propoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide | 215302-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-6-((R)-2,3-Dihydroxy-propoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• 英文别名: N-[(2S,3R,4R,5S,6R)-6-[[(2R)-2,3-dihydroxypropoxy]methyl]-5-hydroxy-2-octoxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 215302-32-2
• 化学式: C₂₅H₄₇NO₁₂
• 分子量: 553.648
• InChiKey: LJMPFUWEXBMPDQ-ATYFKIPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  197
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-6-((R)-2,3-Dihydroxy-propoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以96%的产率得到N-[(2S,3R,4R,5S,6R)-6-((S)-2,3-Dihydroxy-propoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Novel Disaccharide Inhibitors of Human Glioma Cell Division

  摘要：

  Several alpha-L-Fuc-(1-->3)-alpha-D-GlcNAcOC(8)H(17) disaccharide derivatives bearing different hydroxylated alkyl chains, with or without sulfate groups at C-4 and/or C-6 positions of the GlcNAc unit, have been synthesized and-tested as inhibitors of human astrocytoma Lines U-373 and U-118. The antimitotic activity was dependent on the structure and position of the hydroxylated chain linked to the disaccharide. The compounds with a pentaerythritol or L-glyceryl chain at the C-6 position showed the best inhibitory properties, with an ID50 value of ca. 200 mu M. On the contrary, sulfated disaccharide derivatives were inactive. The antimitotic activities of the compounds tested were essentially independent of the mitogen used to stimulate cell division.

  DOI：

  10.1021/jm980365i
• 作为产物：
  描述：

  Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)GlcNAc(a)-O-octyl 在 palladium on activated charcoal 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 12.08h， 生成 N-[(2S,3R,4R,5S,6R)-6-((R)-2,3-Dihydroxy-propoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Novel Disaccharide Inhibitors of Human Glioma Cell Division

  摘要：

  Several alpha-L-Fuc-(1-->3)-alpha-D-GlcNAcOC(8)H(17) disaccharide derivatives bearing different hydroxylated alkyl chains, with or without sulfate groups at C-4 and/or C-6 positions of the GlcNAc unit, have been synthesized and-tested as inhibitors of human astrocytoma Lines U-373 and U-118. The antimitotic activity was dependent on the structure and position of the hydroxylated chain linked to the disaccharide. The compounds with a pentaerythritol or L-glyceryl chain at the C-6 position showed the best inhibitory properties, with an ID50 value of ca. 200 mu M. On the contrary, sulfated disaccharide derivatives were inactive. The antimitotic activities of the compounds tested were essentially independent of the mitogen used to stimulate cell division.

  DOI：

  10.1021/jm980365i