4-benzyl-3-(3,5-dimethylphenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole | 1430730-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzyl-3-(3,5-dimethylphenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole
• 英文别名: 4-benzyl-5-(3,5-dimethylphenyl)-3-(β-D-glucopyranosyl)-1,2,4-triazole；(2S,3R,4R,5S,6R)-2-[4-benzyl-5-(3,5-dimethylphenyl)-1,2,4-triazol-3-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1430730-59-8
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: SUXYDORXVPOBQO-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-benzyl-3-(3,5-dimethylphenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以98%的产率得到3-(3,5-dimethylphenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.02.041
• 作为产物：
  描述：

  4-benzyl-5-(3,5-dimethylphenyl)-3-(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62%的产率得到4-benzyl-3-(3,5-dimethylphenyl)-5-(β-D-glucopyranosyl)-1,2,4-triazole
  参考文献：
  名称：

  New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.02.041

文献信息

• [EN] GLYCOGEN PHOSPHORYLASE INHIBITORS<br/>[FR] INHIBITEURS DE PHOSPHORYLASE DE GLYCOGÈNE
  申请人：DEBRECENI EGYETEM

  公开号：WO2013061105A2

  公开（公告）日：2013-05-02

  The invention relates to compounds of formula (I) and stereoisomers, tautomers and pharmaceutically acceptable salts thereof and processes for preparing them. In formula (I) X is -CH= or -N= or -N(R") -; Y is -N= or -N(R") -; R is an alkyl group, an aryl group or a heteroaryl group, which groups are unsubstituted or substituted; R' is hydrogen or PG1, R" is hydrogen or PG2, R"' is hydrogen or R'OCH2-; n is an integer of 1 to 3. The invention also relates to pharmaceutical compositions containing these compounds. The compounds according to the invention are glycogen phosphorylase inhibitors and can be used e.g. for the treatment of type 2 diabetes, cardiovascular disorders and tumorous growth.˙
• 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.