N-(β-D-glucopyranosyl)-3-(2-naphthyl)isoxazole-5-carboxamide | 1366651-61-7

• 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)-3-(2-naphthyl)isoxazole-5-carboxamide
• 英文别名: 3-naphthalen-2-yl-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,2-oxazole-5-carboxamide
• CAS: 1366651-61-7
• 化学式: C₂₀H₂₀N₂O₇
• 分子量: 400.388
• InChiKey: QAOOYQZZXYFTEP-BFMVXSJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  145
• 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 、 sodium hypochlorite 、 氢气 、 sodium methylate 、 镍 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.5h， 生成 N-(β-D-glucopyranosyl)-3-(2-naphthyl)isoxazole-5-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

文献信息

• Synthesis of heterocyclic N-(β-d-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase
  作者：Bálint Kónya、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2012.01.020

  日期：2012.4

  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.