methyl (benzyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 146369-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (benzyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS: 146369-11-1
• 化学式: C₁₉H₂₆N₄O₈
• 分子量: 438.437
• InChiKey: VGCQTZAGKCMGCU-DWYCWXKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  183.31
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (benzyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到sodium (benzyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of sialic acid derivatives as ligands for the myelin-associated glycoprotein (MAG)

  摘要：

  The trisaccharide substructure 13 of the ganglioside GQ1b alpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 13, sialosides with modifications at the reducing and non-reducing end were synthesized. The biological evaluation of mimics 12a-o was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 12h was enhanced by more than 1000-fold in comparison to the reference trisaccharide 13, despite the former having a much simpler structure. In addition, the sialic acid derivatives, for example, 12h, have clearly improved pharmacokinetic properties due to the presence of aromatic moieties, a lower molecular weight, and a reduced number of polar hydroxy functions compared to the reference compound 13. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.038
• 作为产物：
  描述：

  methyl (benzyl 5-acetamido-3,5-dideoxy-9-O-(4-toluenesulfonyl)-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 sodium azide 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以75%的产率得到methyl (benzyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of sialic acid derivatives as ligands for the myelin-associated glycoprotein (MAG)

  摘要：

  The trisaccharide substructure 13 of the ganglioside GQ1b alpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 13, sialosides with modifications at the reducing and non-reducing end were synthesized. The biological evaluation of mimics 12a-o was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 12h was enhanced by more than 1000-fold in comparison to the reference trisaccharide 13, despite the former having a much simpler structure. In addition, the sialic acid derivatives, for example, 12h, have clearly improved pharmacokinetic properties due to the presence of aromatic moieties, a lower molecular weight, and a reduced number of polar hydroxy functions compared to the reference compound 13. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.038