4-phenyl-1-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl)-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-phenyl-1-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl)-1H-1,2,3-triazole
• 英文别名: 1,2:5,6-di-O-isopropylidene-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-α-D-allofuranose；1-[(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]-4-phenyltriazole
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: RYDMKGGPJHBFRU-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-phenyl-1-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  糖基三唑配体存在下Cu（I）催化C-杂原子偶联反应合成苯并唑

  摘要：

  糖基三唑可以方便地获得，并且包含多个金属结合单元，可以协助金属介导的催化作用。d-葡萄糖的叠氮化物衍生物已被转化为它们各自的芳基三唑，并被筛选为通过铜催化的分子内Ullmann型C-杂原子偶联合成2-取代的苯并稠合的唑和苯并咪唑并喹唑啉酮的配体。对于这种容易获得的催化体系，获得了多种苯并稠合杂环的良好或优异的产率。

  DOI：

  10.1021/acscombsci.9b00004

文献信息

• Synthesis, Biological Activity, and Molecular Modeling Studies of 1<i>H</i>-1,2,3-Triazole Derivatives of Carbohydrates as α-Glucosidases Inhibitors
  作者：Sabrina B. Ferreira、Ana C. R. Sodero、Mariana F. C. Cardoso、Emerson S. Lima、Carlos R. Kaiser、Floriano P. Silva、Vitor F. Ferreira

  DOI：10.1021/jm901265h

  日期：2010.3.25

  A class of drugs in use for treating type II diabetes mellitus (T2D), typified by the pseudotetrasaccharide acarbose, act by inhibiting the a-glucosidase activity present in pancreatic secretions and in the brush border of the small intestine. Herein, we report the synthesis of a series of 4-substituted 1,2,3-triazoles conjugated with sugars, including D-xylose, D-galactose, D-allose, and D-ribose. Compounds were screened for alpha-glucosidase inhibitory activity using yeast maltase (MAL12) as a model enzyme. Methyl-2,3-O-isopropylidene-beta-D-riboluranosides, such as the 4-(1-cyclohexenyl)-1,2,3-triazole derivative, were among the most active compounds, showing up to 25-fold higher inhibitory potency than the complex oligosaccharide acarbose. Docking studies on a MAL12 homology model disclosed a binding mode consistent with a transition-state-mimicking mechanism. Finally, the actual pharmacological potential of this triazole series was demonstrated by the reduction of postprandial blood glucose levels in normal rats. These compounds could represent new chemical scaffolds for developing novel drugs against T2D.