3-phenyl-5-(β-D-xylopyranosyl)-1,2,4-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-5-(β-D-xylopyranosyl)-1,2,4-triazole
• 英文别名: (2S,3R,4S,5R)-2-(3-phenyl-1H-1,2,4-triazol-5-yl)oxane-3,4,5-triol
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: SCVOZHCVTLQOQO-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  n-苄基苯甲酰胺 在 氯化亚砜 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 3-phenyl-5-(β-D-xylopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase

  摘要：

  New derivatives of D-xylose with aglycons of the most efficient glucose derived inhibitors of glycogen phosphorylase were synthesized to explore the specificity of the enzyme towards the structure of the sugar part of the molecules. Thus, 2-(beta-D-xylopyranosyl) benzimidazole and 3-substituted-5-(beta-D-xylopyranosyl)1,2,4-triazoles were obtained in multistep procedures from O-perbenzoylated b-D-xylopyranosyl cyanide. Cycloadditions of nitrile-oxides and O-peracetylated exo-xylal obtained from the corresponding beta-D-xylopyranosyl cyanide furnished xylopyranosylidene-spiro-isoxazoline derivatives. Oxidative ring closure of O-peracetylated beta-D-xylopyranosyl-thiohydroximates prepared from 1-thio-beta-D-xylopyranose and nitrile-oxides gave xylopyranosylidene-spiro-oxathiazoles. The fully deprotected test compounds were assayed against rabbit muscle glycogen phosphorylase b to show moderate inhibition for 3-(2-naphthyl)-5-(beta-D-xylopyranosyl)-1,2,4-triazole (IC50 = 0.9 mM) only. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.020

文献信息

• [EN] GLYCOGEN PHOSPHORYLASE INHIBITORS<br/>[FR] INHIBITEURS DE PHOSPHORYLASE DE GLYCOGÈNE
  申请人：DEBRECENI EGYETEM

  公开号：WO2013061105A8

  公开（公告）日：2013-09-19
• Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase
  作者：László Somsák、Éva Bokor、Beáta Czibere、Katalin Czifrák、Csenge Koppány、László Kulcsár、Sándor Kun、Enikő Szilágyi、Marietta Tóth、Tibor Docsa、Pál Gergely

  DOI：10.1016/j.carres.2014.05.020

  日期：2014.11

  New derivatives of D-xylose with aglycons of the most efficient glucose derived inhibitors of glycogen phosphorylase were synthesized to explore the specificity of the enzyme towards the structure of the sugar part of the molecules. Thus, 2-(beta-D-xylopyranosyl) benzimidazole and 3-substituted-5-(beta-D-xylopyranosyl)1,2,4-triazoles were obtained in multistep procedures from O-perbenzoylated b-D-xylopyranosyl cyanide. Cycloadditions of nitrile-oxides and O-peracetylated exo-xylal obtained from the corresponding beta-D-xylopyranosyl cyanide furnished xylopyranosylidene-spiro-isoxazoline derivatives. Oxidative ring closure of O-peracetylated beta-D-xylopyranosyl-thiohydroximates prepared from 1-thio-beta-D-xylopyranose and nitrile-oxides gave xylopyranosylidene-spiro-oxathiazoles. The fully deprotected test compounds were assayed against rabbit muscle glycogen phosphorylase b to show moderate inhibition for 3-(2-naphthyl)-5-(beta-D-xylopyranosyl)-1,2,4-triazole (IC50 = 0.9 mM) only. (C) 2014 Elsevier Ltd. All rights reserved.