N-(β-D-glucopyranosyl)-1-(2-naphthyl)-1,2,3-triazole-4-carboxamide | 1366651-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(β-D-glucopyranosyl)-1-(2-naphthyl)-1,2,3-triazole-4-carboxamide
• 英文别名: 1-naphthalen-2-yl-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazole-4-carboxamide
• CAS: 1366651-41-3
• 化学式: C₁₉H₂₀N₄O₆
• 分子量: 400.391
• InChiKey: IWICNEPZYDMMOT-OGJJZOIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  150
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 甲醇 、 copper(ll) sulfate pentahydrate 、 氢气 、 sodium methylate 、 镍 、 N,N'-二环己基碳二亚胺 、 维生素 C 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 N-(β-D-glucopyranosyl)-1-(2-naphthyl)-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  Synthesis of heterocyclic N-(β-d-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase

  摘要：

  In a DCC-mediated coupling 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine and propiolic acid gave N-propynoyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine which was transformed by 1,3-dipolar cycloadditions with aromatic azides and nitrile-oxides to the corresponding O-peracetylated N-(beta-D-glucopyranosyl)-1-substituted-1,2,3-triazole-4-carboxamides and N-(beta-D-glucopyranosyl)-3-substitutedisoxazole-5-carboxamides, respectively. These compounds were O-deacetylated by Zemplen's protocol to be tested as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitors of the two series were N-(beta-D-glucopyranosyl)-1-(3,5-dimethyl-phenyl)-1,2,3-triazole-4-carboxamide (K-i = 34 mu M) and N-(beta-D-glucopyranosyl)-3-(indol-2-yl)-isoxazole-5-carboxamide (K-i = 164 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.020