(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine | 1300698-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
• CAS: 1300698-50-3
• 化学式: C₄₅H₄₂N₂O₄
• 分子量: 674.839
• InChiKey: XVGXUWWJRAFWJF-GKNWPNITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 在 palladium on carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、600.01 kPa 条件下， 反应 56.0h， 以71%的产率得到(5R,6R,7S,8S)-5-(hydroxymethyl)-2-(4-methylphenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
  参考文献：
  名称：

  Structure–activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors

  摘要：

  Inhibition of glycoside hydrolases has widespread application in treatment of diabetes, viral infections, lysosomal storage diseases and cancers. Gluco-configured tetrahydroimidazopyridines are the most potent beta-glucosidase inhibitors reported to date. Using transition state mimic strategy, a series of C2-substituted gluco-configured tetrahydroimidazopyridines were designed and synthesized. Compounds 3 (K-i = 0.64 nM) and 5 (K-i = 0.58 nM) showed stronger inhibitory potency against beta-glucosidase. Maestro 9.1 was used to study the structure-activity relationships by docking the compounds into the beta-glucosidase active sites. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.043
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-glucono-δ-thiolactam 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 乙基溴化镁 、 mercury(II) diacetate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(2-(4-methylphenyl)ethynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Structure–activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors

  摘要：

  Inhibition of glycoside hydrolases has widespread application in treatment of diabetes, viral infections, lysosomal storage diseases and cancers. Gluco-configured tetrahydroimidazopyridines are the most potent beta-glucosidase inhibitors reported to date. Using transition state mimic strategy, a series of C2-substituted gluco-configured tetrahydroimidazopyridines were designed and synthesized. Compounds 3 (K-i = 0.64 nM) and 5 (K-i = 0.58 nM) showed stronger inhibitory potency against beta-glucosidase. Maestro 9.1 was used to study the structure-activity relationships by docking the compounds into the beta-glucosidase active sites. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.043