2-(β-D-xylopyranosyl)benzimidazole | 1245210-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(β-D-xylopyranosyl)benzimidazole
• 英文别名: 2-(beta-d-Xylopyranosyl)benzimidazole；(2S,3R,4S,5R)-2-(1H-benzimidazol-2-yl)oxane-3,4,5-triol
• CAS: 1245210-78-9
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: OMNRFAPXSXSWNL-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.6
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)benzimidazole 以 甲醇 为溶剂， 生成 2-(β-D-xylopyranosyl)benzimidazole
  参考文献：
  名称：

  通过吡喃糖基腈氧化物的亲核加成反应合成2-吡喃基苯并噻唑，苯并咪唑和苯并恶唑

  摘要：

  通过相应的羟基氧酰氯的脱氯化氢反应生成的过-O-乙酰化的β- d-吡喃基腈腈氧化物与2-氨基硫酚反应，得到2-（β- d-吡喃基）苯并噻唑。1,2-二氨基苯和2-氨基苯酚的反应相似，分别得到2-（β- d-吡喃基）苯并咪唑和2-（β- d-吡喃基）苯并恶唑。的2-β-结构d -glucopyranosylbenzimidazole（17），2-（2,3,4-三- ø -乙酰基β- d -xylopyranosyl）苯并咪唑（19）和所述thiohydroximate吡喃木糖13 是由X射线建立晶体学。

  DOI：

  10.1016/j.tet.2010.06.076

文献信息

• 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.