3-methyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole | 1430731-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole
• CAS: 1430731-51-3
• 化学式: C₃₇H₃₁N₃O₉
• 分子量: 661.668
• InChiKey: BOUHQOUDGCAAAR-HXBJCGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  156.0
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-methyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 72.0h， 以73%的产率得到5-(β-D-glucopyranosyl)-3-methyl-1,2,4-triazole
  参考文献：
  名称：

  [EN] GLYCOGEN PHOSPHORYLASE INHIBITORS
  [FR] INHIBITEURS DE PHOSPHORYLASE DE GLYCOGÈNE

  摘要：

  公开号：

  WO2013061105A8
• 作为产物：
  描述：

  ethyl C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)formimidate 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 120.0h， 生成 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

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。
• New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase
  作者：Sándor Kun、Éva Bokor、Gergely Varga、Béla Szőcs、András Páhi、Katalin Czifrák、Marietta Tóth、László Juhász、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.ejmech.2014.02.041

  日期：2014.4

  O-Perbenzoylated 5-(beta-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (K-i 0.67 mu M) and the 5-(2-naphthyl)-substituted (K-i 0.41 mu M) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. (C) 2014 Elsevier Masson SAS. All rights reserved.