3-(4-aminophenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole | 1430730-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-aminophenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole
• 英文别名: 5-(4-aminophenyl)-3-(β-D-glucopyranosyl)-1,2,4-triazole；(2~{S},3~{R},4~{R},5~{S},6~{R})-2-[5-(4-aminophenyl)-4~{H}-1,2,4-triazol-3-yl]-6-(hydroxymethyl)oxane-3,4,5-triol；(2S,3R,4R,5S,6R)-2-[3-(4-aminophenyl)-1H-1,2,4-triazol-5-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1430730-87-2
• 化学式: C₁₄H₁₈N₄O₅
• 分子量: 322.321
• InChiKey: NDNZXPQRERAKKG-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-(β-D-glucopyranosyl)-3-(4-nitrophenyl)-1,2,4-triazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到3-(4-aminophenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  [EN] GLYCOGEN PHOSPHORYLASE INHIBITORS
  [FR] INHIBITEURS DE PHOSPHORYLASE DE GLYCOGÈNE

  摘要：

  公开号：

  WO2013061105A8

文献信息

• New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase
  作者：Sándor Kun、Éva Bokor、Gergely Varga、Béla Szőcs、András Páhi、Katalin Czifrák、Marietta Tóth、László Juhász、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.ejmech.2014.02.041

  日期：2014.4

  O-Perbenzoylated 5-(beta-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (K-i 0.67 mu M) and the 5-(2-naphthyl)-substituted (K-i 0.41 mu M) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. (C) 2014 Elsevier Masson SAS. All rights reserved.