N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2H-tetrazole-5-carboxamide | 1453191-52-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2H-tetrazole-5-carboxamide
• CAS: 1453191-52-0
• 化学式: C₁₆H₂₁N₅O₁₀
• 分子量: 443.37
• InChiKey: DCBGRULOQZSQIG-GUYIQFIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.99
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  197.99
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2H-tetrazole-5-carboxamide 在 甲醇 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 N-(β-D-glucopyranosyl) 5-(naphth-2-yl)-1,3,4-oxadiazol-2-carboxamide
  参考文献：
  名称：

  Synthesis, enzyme kinetics and computational evaluation of N-(β-d-glucopyranosyl) oxadiazolecarboxamides as glycogen phosphorylase inhibitors

  摘要：

  All possible isomers of N-beta-D-glucopyranosyl aryl-substituted oxadiazolecarboxamides were synthesised. O-Peracetylated N-cyanocarbonyl-beta-D-glucopyranosylamine was transformed into the corresponding N-glucosyl tetrazole-5-carboxamide, which upon acylation gave N-glucosyl 5-ary1-1,3,4-oxadiazole-2-carboxamides. The nitrite group of the N-cyanocarbonyl derivative was converted to amidoxime which was ring closed by acylation to N-glucosyl 5-aryl-1,2,4-oxadiazole-3-carboxamides. A one-pot reaction of protected beta-D-glucopyranosylamine with oxalyl chloride and then with arenecarboxamidoximes furnished N-glucosyl 3-aryl-1,2,4-oxadiazole-5-carboxamides. Removal of the O-acetyl protecting groups by the Zemplen Method produced test compounds which were evaluated as inhibitors of glycogen phosphorylase. Best inhibitors of these series were N-(beta-D-glucopyranosyl) 5-(naphth-1-yl)-1,2,4-oxadiazol-3-carboxamide (K-i = 30 mu M), N-(beta-D-glucopyranosyl) 5-(naphth-2-y1)-1,3,4-oxadiazol-2-carboxamide (K-i= 33 mu M), and N-(beta-D-glucopyranosyl) 3-phenyl-1,2,4-oxadiazol-5-carboxamide (K-i= 104 mu M). ADMET property predictions revealed these compounds to have promising oral drug-like properties without any toxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.024
• 作为产物：
  描述：

  N-cyanocarbonyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-amine 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 以88%的产率得到N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2H-tetrazole-5-carboxamide
  参考文献：
  名称：

  Synthesis, enzyme kinetics and computational evaluation of N-(β-d-glucopyranosyl) oxadiazolecarboxamides as glycogen phosphorylase inhibitors

  摘要：

  All possible isomers of N-beta-D-glucopyranosyl aryl-substituted oxadiazolecarboxamides were synthesised. O-Peracetylated N-cyanocarbonyl-beta-D-glucopyranosylamine was transformed into the corresponding N-glucosyl tetrazole-5-carboxamide, which upon acylation gave N-glucosyl 5-ary1-1,3,4-oxadiazole-2-carboxamides. The nitrite group of the N-cyanocarbonyl derivative was converted to amidoxime which was ring closed by acylation to N-glucosyl 5-aryl-1,2,4-oxadiazole-3-carboxamides. A one-pot reaction of protected beta-D-glucopyranosylamine with oxalyl chloride and then with arenecarboxamidoximes furnished N-glucosyl 3-aryl-1,2,4-oxadiazole-5-carboxamides. Removal of the O-acetyl protecting groups by the Zemplen Method produced test compounds which were evaluated as inhibitors of glycogen phosphorylase. Best inhibitors of these series were N-(beta-D-glucopyranosyl) 5-(naphth-1-yl)-1,2,4-oxadiazol-3-carboxamide (K-i = 30 mu M), N-(beta-D-glucopyranosyl) 5-(naphth-2-y1)-1,3,4-oxadiazol-2-carboxamide (K-i= 33 mu M), and N-(beta-D-glucopyranosyl) 3-phenyl-1,2,4-oxadiazol-5-carboxamide (K-i= 104 mu M). ADMET property predictions revealed these compounds to have promising oral drug-like properties without any toxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.024

文献信息

• Computationally motivated synthesis and enzyme kinetic evaluation of N-(β-<scp>d</scp>-glucopyranosyl)-1,2,4-triazolecarboxamides as glycogen phosphorylase inhibitors
  作者：Jaida Begum、Gergely Varga、Tibor Docsa、Pál Gergely、Joseph M. Hayes、László Juhász、László Somsák

  DOI：10.1039/c4md00335g

  日期：——

  N-(β-d-Glucopyranosyl)-1,2,4-triazolecarboxamides discovered as low μM inhibitors of glycogen phosphorylase b.

  N-(β-D-葡萄糖吡喃糖苷)-1,2,4-三唑羧酰胺被发现为糖原磷酸化酶b的低μM抑制剂。