5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazole | 1430730-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazole
• 英文别名: 3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-5-phenyl-1,2,4-triazole；[(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-(3-phenyl-1H-1,2,4-triazol-5-yl)oxan-2-yl]methyl benzoate
• CAS: 1430730-66-7
• 化学式: C₄₂H₃₃N₃O₉
• 分子量: 723.739
• InChiKey: RRBCDUKBAPXXMA-SQGINLDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazole 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 72.0h， 以62%的产率得到5-(β-D-glucopyranosyl)-3-phenyl-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：

  (2R,3R,4R,5S,6S)-2-[(苯甲酰氧基)甲基]-6-氰基四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazole
  参考文献：
  名称：

  合成5-芳基-3- Ç -glycosyl-和从亚烷基-氨基腙不对称3,5-二芳基1,2,4-三唑†

  摘要：

  在具有多种生物活性的1,2,4-三唑衍生物中，3 - C-吡喃葡萄糖基-5-取代的1,2,4-三唑属于糖原磷酸化酶的最有效抑制剂，因此是潜在的降糖药。在寻找用于这类化合物的新的合成方法中，研究了N 1-亚烷基羧酰胺dra的氧化性闭环。在NaH 2 PO 2存在下，通过Raney-Ni®还原反应，由相应的糖基氰化物和酰氨基prepared酰胺制备O-酰化的N 1-（β- D-甘氨酸金烷基糖基亚甲基）-芳族羧酰胺基酮。通过NBS对如此获得的化合物进行溴化得到了酰肼基溴化物型衍生物，其在吡啶中或在AcOH中通过NH 4 OAc与3- C-糖基-5-取代-1,2,4-三唑闭环。在相同条件下ø -perbenzoylated Ñ 1 -arylidene- Ç - （β- d吡喃葡萄糖基）-formamidrazones给出预期的-1,2,4-三唑作为只有轻微的产品。N 1-亚芳基-亚芳基甲酰胺还与NBS

  DOI：

  10.1039/c5ra05702g

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
• <i>C</i>-Glucopyranosyl-1,2,4-triazoles As New Potent Inhibitors of Glycogen Phosphorylase
  作者：Éva Bokor、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1021/ml4001529

  日期：2013.7.11

  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).
• 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.
• Synthesis of 5-aryl-3-C-glycosyl- and unsymmetrical 3,5-diaryl-1,2,4-triazoles from alkylidene-amidrazones
  作者：Béla Szőcs、Éva Bokor、Katalin E. Szabó、Attila Kiss-Szikszai、Marietta Tóth、László Somsák

  DOI：10.1039/c5ra05702g

  日期：——

  Bromination of the so obtained compounds by NBS gave hydrazonoyl bromide type derivatives which were ring closed to 3-C-glycosyl-5-substituted-1,2,4-triazoles in pyridine or by NH4OAc in AcOH. Under the same conditions O-perbenzoylated N1-arylidene-C-(β-D-glucopyranosyl)-formamidrazones gave the expected 1,2,4-triazoles as minor products only. N1-Arylidene-arenecarboxamidrazones were also transformed

  在具有多种生物活性的1,2,4-三唑衍生物中，3 - C-吡喃葡萄糖基-5-取代的1,2,4-三唑属于糖原磷酸化酶的最有效抑制剂，因此是潜在的降糖药。在寻找用于这类化合物的新的合成方法中，研究了N 1-亚烷基羧酰胺dra的氧化性闭环。在NaH 2 PO 2存在下，通过Raney-Ni®还原反应，由相应的糖基氰化物和酰氨基prepared酰胺制备O-酰化的N 1-（β- D-甘氨酸金烷基糖基亚甲基）-芳族羧酰胺基酮。通过NBS对如此获得的化合物进行溴化得到了酰肼基溴化物型衍生物，其在吡啶中或在AcOH中通过NH 4 OAc与3- C-糖基-5-取代-1,2,4-三唑闭环。在相同条件下ø -perbenzoylated Ñ 1 -arylidene- Ç - （β- d吡喃葡萄糖基）-formamidrazones给出预期的-1,2,4-三唑作为只有轻微的产品。N 1-亚芳基-亚芳基甲酰胺还与NBS