C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidine | 1430730-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidine
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-carbamimidoyloxan-2-yl]methyl benzoate
• CAS: 1430730-33-8
• 化学式: C₃₅H₃₀N₂O₉
• 分子量: 622.631
• InChiKey: SAFTULAICUPVGK-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidine 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以60%的产率得到N-benzoyl-C-(3,4,6-tri-O-benzoyl-β-D-glucopyranosyl)formamidine
  参考文献：
  名称：

  4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase

  摘要：

  Inhibition of glycogen phosphorylases may lead to pharmacological treatments of diseases in which glycogen metabolism plays an important role: first of all in diabetes, but also in cardiovascular and tumorous disorders. C-(beta-D-Glucopyranosyl) isoxazole, pyrazole, thiazole, and imidazole type compounds were synthesized, and the latter showed the strongest inhibition against rabbit muscle glycogen phosphorylase b. Most efficient was 2-(beta-D-glucopyranosyl)-4(5)-(2-naphthyl)-imidazole (11b, K-i = 31 nM) representing the best nanomolar glucose derived inhibitor of the enzyme.

  DOI：

  10.1021/acsmedchemlett.5b00361
• 作为产物：
  描述：

  C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidoxime 在 乙酸酐 、 溶剂黄146 、 甲酸 、 palladium 10% on activated carbon 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以61%的产率得到C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formamidine
  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

• [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
• 4(5)-Aryl-2-<i>C</i>-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase
  作者：Éva Bokor、Sándor Kun、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1021/acsmedchemlett.5b00361

  日期：2015.12.10

  Inhibition of glycogen phosphorylases may lead to pharmacological treatments of diseases in which glycogen metabolism plays an important role: first of all in diabetes, but also in cardiovascular and tumorous disorders. C-(beta-D-Glucopyranosyl) isoxazole, pyrazole, thiazole, and imidazole type compounds were synthesized, and the latter showed the strongest inhibition against rabbit muscle glycogen phosphorylase b. Most efficient was 2-(beta-D-glucopyranosyl)-4(5)-(2-naphthyl)-imidazole (11b, K-i = 31 nM) representing the best nanomolar glucose derived inhibitor of the enzyme.