5(6)-fluoro-2-(3',4',6'-tri-O-benzoyl-2'-deoxy-D-arabino-hex-1-enopyranosyl)benzimidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5(6)-fluoro-2-(3',4',6'-tri-O-benzoyl-2'-deoxy-D-arabino-hex-1-enopyranosyl)benzimidazole
• 英文别名: [(2R,3S,4R)-3,4-dibenzoyloxy-6-(6-fluoro-1H-benzimidazol-2-yl)-3,4-dihydro-2H-pyran-2-yl]methyl benzoate
• 化学式: C₃₄H₂₅FN₂O₇
• 分子量: 592.58
• InChiKey: CLZNTOVHPJMSGN-NNFJYWIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-[(苯甲酰氧基)甲基]-6-氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 以 二氯甲烷 为溶剂， 反应 53.0h， 生成 5(6)-fluoro-2-(3',4',6'-tri-O-benzoyl-2'-deoxy-D-arabino-hex-1-enopyranosyl)benzimidazole 、 5(6)-fluoro-2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)benzimidazole
  参考文献：
  名称：

  Synthesis of substituted 2-(β-d-glucopyranosyl)-benzimidazoles and their evaluation as inhibitors of glycogen phosphorylase

  摘要：

  Microwave assisted condensation of O-perbenzoylated C-(beta-D-glucopyranosyl) formic acid with 1,2-diaminobenzenes in the presence of triphenylphosphite gave the corresponding O-protected 2-(beta-D-glucopyranosyl)-benzimidazoles in moderate yields. O-Perbenzoylated C-(beta-D-glucopyranosyl) formamide and -thioformamide were transformed into the corresponding ethyl C-(beta-D-glucopyranosyl) formimidate and -thioformimidate, respectively, by Et3O center dot BF4. Treatment of the formimidate with 1,2-diaminobenzenes afforded O-protected 2-(beta-D-glucopyranosyl)-benzimidazoles in good to excellent yields. Similar reaction of the thioformimidate gave these compounds in lower yields. The O-benzoyl protecting groups were removed by the Zemplen protocol. These test compounds were assayed against rabbit muscle glycogen phosphorylase (GP) b, the prototype of liver GP, the rate limiting enzyme of glycogen degradation. The best inhibitors were 2-(beta-D-glucopyranosyl)-4-methyl-benzimidazole (K-i = 2.8 mu M) and 2-(beta-D-glucopyranosyl)- naphtho[2,3-d] imidazole (K-i = 2.1 mu M) exhibiting a similar to 3-4 times stronger binding than the unsubstituted parent compound. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.01.011

文献信息

• Synthesis of substituted 2-(β-d-glucopyranosyl)-benzimidazoles and their evaluation as inhibitors of glycogen phosphorylase
  作者：Éva Bokor、Enikő Szilágyi、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2013.01.011

  日期：2013.11

  Microwave assisted condensation of O-perbenzoylated C-(beta-D-glucopyranosyl) formic acid with 1,2-diaminobenzenes in the presence of triphenylphosphite gave the corresponding O-protected 2-(beta-D-glucopyranosyl)-benzimidazoles in moderate yields. O-Perbenzoylated C-(beta-D-glucopyranosyl) formamide and -thioformamide were transformed into the corresponding ethyl C-(beta-D-glucopyranosyl) formimidate and -thioformimidate, respectively, by Et3O center dot BF4. Treatment of the formimidate with 1,2-diaminobenzenes afforded O-protected 2-(beta-D-glucopyranosyl)-benzimidazoles in good to excellent yields. Similar reaction of the thioformimidate gave these compounds in lower yields. The O-benzoyl protecting groups were removed by the Zemplen protocol. These test compounds were assayed against rabbit muscle glycogen phosphorylase (GP) b, the prototype of liver GP, the rate limiting enzyme of glycogen degradation. The best inhibitors were 2-(beta-D-glucopyranosyl)-4-methyl-benzimidazole (K-i = 2.8 mu M) and 2-(beta-D-glucopyranosyl)- naphtho[2,3-d] imidazole (K-i = 2.1 mu M) exhibiting a similar to 3-4 times stronger binding than the unsubstituted parent compound. (C) 2013 Elsevier Ltd. All rights reserved.