1-(β-D-glucopyranosyl)-4-(1-naphthyl)-1,2,3-triazole | 1169566-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-glucopyranosyl)-4-(1-naphthyl)-1,2,3-triazole
• 英文别名: 1-beta-D-glucopyranosyl-4-naphthalen-1-yl-1H-1,2,3-triazole；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-naphthalen-1-yltriazol-1-yl)oxane-3,4,5-triol
• CAS: 1169566-52-2
• 化学式: C₁₈H₁₉N₃O₅
• 分子量: 357.366
• InChiKey: ZQSWMZLNZOWSSB-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(1-naphthyl)-1,2,3-triazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到1-(β-D-glucopyranosyl)-4-(1-naphthyl)-1,2,3-triazole
  参考文献：
  名称：

  Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case

  摘要：

  Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished beta-D-Glc(p)-NHCO-R derivatives as well as 1-(beta-D-Glc(p))-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.021

文献信息

• Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case
  作者：Evangelia D. Chrysina、Éva Bokor、Kyra-Melinda Alexacou、Maria-Despoina Charavgi、George N. Oikonomakos、Spyros E. Zographos、Demetres D. Leonidas、Nikos G. Oikonomakos、László Somsák

  DOI：10.1016/j.tetasy.2009.03.021

  日期：2009.5

  Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished beta-D-Glc(p)-NHCO-R derivatives as well as 1-(beta-D-Glc(p))-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of 1-(d-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors
  作者：Éva Bokor、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.bmc.2009.12.043

  日期：2010.2

  1-(D-Glucopyranosyl)-1,2,3-triazoles were prepared from per-O-acetylated alpha-and beta-D-glucopyranosyl azides as well as per-O-benzoylated (beta-D-gluco-hept-2-ulopyranosylazide)onamide and onic acid methylester by using azide-alkyne cycloaddition catalysed by in situ generated Cu(I) under aqueous conditions. The O-acyl protecting groups were removed by the Zemplen protocol. The test compounds were assayed against rabbit muscle glycogen phosphorylase b to show that the b-D-glucopyranosyl derivatives were superior inhibitors as compared to the two other series of triazoles. (C) 2009 Elsevier Ltd. All rights reserved.