N-(β-D-glucopyranosyl)-3-(1,3-benzothiazol-2-yl)isoxazole-5-carboxamide | 1366651-65-1

• 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-(1,3-benzothiazol-2-yl)isoxazole-5-carboxamide
• CAS: 1366651-65-1
• 化学式: C₁₇H₁₇N₃O₇S
• 分子量: 407.404
• InChiKey: RIQXQWFTGALUHX-RSQMQNDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.52
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  158.17
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 在 甲醇 、 sodium hypochlorite 、 sodium methylate 、 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 18.0h， 生成 N-(β-D-glucopyranosyl)-3-(1,3-benzothiazol-2-yl)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