(2R,3S,4R)-2-azidomethyl-3,4-O-isopropylidene-pyrrolidine-3,4-diol | 1207676-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-2-azidomethyl-3,4-O-isopropylidene-pyrrolidine-3,4-diol
• 英文别名: (3aS,4R,6aR)-4-(azidomethyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole；(3aS,4R,6aR)-4-(azidomethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 1207676-13-8
• 化学式: C₈H₁₄N₄O₂
• 分子量: 198.225
• InChiKey: UIRQGJNKEYFHKO-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2-azidomethyl-3,4-O-isopropylidene-pyrrolidine-3,4-diol 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (2R,3S,4R)-2-[((4-(6-methoxynaphthalen-2-yl)-1H-1,2,3-triazol-1-yl)methyl)]-pyrrolidine-3,4-diol
  参考文献：
  名称：

  Tuning of β-glucosidase and α-galactosidase inhibition by generation and in situ screening of a library of pyrrolidine-triazole hybrid molecules

  摘要：

  The preliminary screening of two libraries of epimeric (pyrrolidin-2-yl)triazoles (14a-s and 22a-s), generated via click chemistry, allowed the rapid identification of four alpha-galactosidase (coffee beans) inhibitors (22b,k,p,r) and two beta-glucosidase (almond) inhibitors (14b,f) in the low mu M range. The additional biological analysis of 14b,f towards beta-glucocerebrosidase (human lysosomal beta-glucosidase), as target enzyme for Gaucher disease, showed a good correlation with the inhibition results obtained for the plant (almond) enzyme. Surprisingly, although these compounds showed inhibition towards beta-glucocerebrosidase as acid hydrolase, they did not inhibit bovine liver beta-glucosidase as neutral hydrolase. In contrast to what was observed for beta-glucosidase inhibition, the coffee bean alpha-galactosidase inhibitors of the epimeric library (22b,k,p,r) only showed weak inhibition towards human lysosomal alpha-galactosidase. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.06.055
• 作为产物：
  描述：

  (2R,3S,4R)-N-tert-butoxycarbonyl-5-hydroxymethyl-3,4-isopropylidenedioxy-pyrrolidine 在 吡啶 、 叠氮化四丁基铵 作用下， 以 四氢呋喃 为溶剂， 反应 336.0h， 生成 (2R,3S,4R)-2-azidomethyl-3,4-O-isopropylidene-pyrrolidine-3,4-diol
  参考文献：
  名称：

  Tuning of β-glucosidase and α-galactosidase inhibition by generation and in situ screening of a library of pyrrolidine-triazole hybrid molecules

  摘要：

  The preliminary screening of two libraries of epimeric (pyrrolidin-2-yl)triazoles (14a-s and 22a-s), generated via click chemistry, allowed the rapid identification of four alpha-galactosidase (coffee beans) inhibitors (22b,k,p,r) and two beta-glucosidase (almond) inhibitors (14b,f) in the low mu M range. The additional biological analysis of 14b,f towards beta-glucocerebrosidase (human lysosomal beta-glucosidase), as target enzyme for Gaucher disease, showed a good correlation with the inhibition results obtained for the plant (almond) enzyme. Surprisingly, although these compounds showed inhibition towards beta-glucocerebrosidase as acid hydrolase, they did not inhibit bovine liver beta-glucosidase as neutral hydrolase. In contrast to what was observed for beta-glucosidase inhibition, the coffee bean alpha-galactosidase inhibitors of the epimeric library (22b,k,p,r) only showed weak inhibition towards human lysosomal alpha-galactosidase. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.06.055