3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-methyl-1-tosyl-1,2,4-triazole | 1430730-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-methyl-1-tosyl-1,2,4-triazole
• 英文别名: 5-methyl-3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1-tosyl-1,2,4-triazole
• CAS: 1430730-65-6
• 化学式: C₄₄H₃₇N₃O₁₁S
• 分子量: 815.857
• InChiKey: QSAFBFAAHKNXAE-GFRPZHATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  59.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  179.28
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-methyl-1-tosyl-1,2,4-triazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到3-methyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  C-Glucopyranosyl-1,2,4-triazoles As New Potent Inhibitors of Glycogen Phosphorylase

  摘要：

  Glycogen phosphorylase inhibitors are considered as potential antidiabetic agents. 3-(beta-D-Glucopyranosyl)-5-substituted-1,2,4-triazoles were prepared by acylation of O-perbenzoylated N-1-tosyl-C-beta-D-glucopyranosyl formamidrazone and subsequent removal of the protecting groups. The best inhibitor was 3-(beta-D-glucopyranosyl)-5-(2-naphthyl)-1,2,4-triazole (K-i = 0.41 mu M against rabbit muscle glycogen phosphorylase b).

  DOI：

  10.1021/ml4001529
• 作为产物：
  描述：

  对甲苯磺酰肼 在 吡啶 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 120.0h， 生成 3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-methyl-1-tosyl-1,2,4-triazole
  参考文献：
  名称：

  C-Glucopyranosyl-1,2,4-triazoles As New Potent Inhibitors of Glycogen Phosphorylase

  摘要：

  Glycogen phosphorylase inhibitors are considered as potential antidiabetic agents. 3-(beta-D-Glucopyranosyl)-5-substituted-1,2,4-triazoles were prepared by acylation of O-perbenzoylated N-1-tosyl-C-beta-D-glucopyranosyl formamidrazone and subsequent removal of the protecting groups. The best inhibitor was 3-(beta-D-glucopyranosyl)-5-(2-naphthyl)-1,2,4-triazole (K-i = 0.41 mu M against rabbit muscle glycogen phosphorylase b).

  DOI：

  10.1021/ml4001529

文献信息

• C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-d-glucopyranosyl-1,5-disubstituted and 5-β-d-glucopyranosyl-1,3-disubstituted variants
  作者：Katalin E. Szabó、András Páhi、László Somsák

  DOI：10.1016/j.tet.2017.05.014

  日期：2017.7

  Highly variable synthetic routes were elaborated toward trisubstituted C-glycopyranosyl 1,2,4-triazoles. N-Acyl-thioamide derivatives were obtained by acylation of O-perbenzoylated 2,6-anhydro-d-glycero-d-gulo-heptonothioamide by acid chlorides and of thioamides by O-perbenzoylated 2,6-anhydro-d-glycero-d-gulo-heptonoyl chloride. These precursors reacted with substituted hydrazines in a regioselective

  精心设计了高度可变的合成路线，以形成三取代的C-甘露糖基1,2,4-三唑。Ñ酰基硫代酰胺衍生物通过酰化得到ö -perbenzoylated 2,6-脱水- d -甘油基- d -庚糖酸氯化物和硫代酰胺通过-heptonothioamide ö -perbenzoylated 2,6-脱水- d -甘油基- d -庚-heptonoyl酰氯。这些前体以区域选择性的方式与取代的肼反应，生成3-β- d-吡喃葡萄糖基-1,5-二取代-和5-β- d-吡喃葡萄糖基-1,3-二取代-1,2,4-三唑。类似的N-酰基-2，6-脱水庚酰胺不能使上述三唑与肼结合。通过Zemplén方法对C-葡萄糖基1,2,4-三唑进行O-脱保护，得到的测试化合物没有抑制兔肌肉糖原磷酸化酶b的作用。
• [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