N-cyclohexyl-N-(2-oxo-2-((((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)amino)ethyl)acetamide | 857843-49-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-cyclohexyl-N-(2-oxo-2-((((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)amino)ethyl)acetamide
• CAS: 857843-49-3
• 化学式: C₁₇H₃₀N₂O₇
• 分子量: 374.434
• InChiKey: DQYHEFFOIRIJAO-ZUOZUFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  128.56
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-N-(2-oxo-2-((((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)amino)ethyl)acetamide 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 PG2072
  参考文献：
  名称：

  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

  摘要：

  A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of D-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.001
• 作为产物：
  描述：

  methyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranoside 在 Pd(OH)2/C 、 氢气 、 乙酸酐 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 18.0 ℃ 、344.75 kPa 条件下， 反应 50.5h， 生成 N-cyclohexyl-N-(2-oxo-2-((((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)amino)ethyl)acetamide
  参考文献：
  名称：

  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

  摘要：

  A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of D-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.001