(5R,6R,7S,8S)-6,8-bis(benzyloxy)-5-((benzyloxy)methyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-7-ol

• 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)-6,8-bis(benzyloxy)-5-((benzyloxy)methyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-7-ol
• 英文别名: (5R,6R,7S,8S)-6,8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-7-ol
• 化学式: C₂₉H₃₀N₂O₄
• 分子量: 470.568
• InChiKey: PJEWOKWXKDZJBC-JUDWXZBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,6R,7S,8S)-6,8-bis(benzyloxy)-5-((benzyloxy)methyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-7-ol 在 sodium hexamethyldisilazane 、 caesium carbonate 、 对硝基苯甲酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (5R,6R,7R,8S)-6,8-bis(benzyloxy)-5-((benzyloxy)methyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-7-ol
  参考文献：
  名称：

  Synthesis and evaluation of 3-deoxy and 3-deoxy-3-fluoro derivatives of gluco- and manno-configured tetrahydropyridoimidazole glycosidase inhibitors

  摘要：

  Three tetrahydropyridoimidazole-type glycosidase inhibitors have been synthesized with the 3-deoxy ribo-and arabino-, and 3-deoxy-3-fluoro gluco-configurations and two of them screened for activity against alpha- and beta-gluco-and mannosidase enzymes. Only one substance, the 3-deoxy-3-fluoro-derivative of the gluco-configured tetrahydropyridoimidazole was found to have any activity against a single enzyme, sweet almond beta-glucosidase, and even then at a level 100-fold lower than that of the corresponding simple gluco-configured tetrahydropyridoimidazole thereby underlining the importance of the 3-hydroxy group in the key substrate-enzyme interactions. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.011
• 作为产物：
  描述：

  (5R,6R,7S,8S)-7-(2-naphthylmethyl)-6,8-bis(benzyloxy)-5-(benzyloxy)methyl-5,6,7,8-tetrahydroimidazo1,2-apyridine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 以53%的产率得到(5R,6R,7S,8S)-6,8-bis(benzyloxy)-5-((benzyloxy)methyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-7-ol
  参考文献：
  名称：

  Synthesis and evaluation of 3-deoxy and 3-deoxy-3-fluoro derivatives of gluco- and manno-configured tetrahydropyridoimidazole glycosidase inhibitors

  摘要：

  Three tetrahydropyridoimidazole-type glycosidase inhibitors have been synthesized with the 3-deoxy ribo-and arabino-, and 3-deoxy-3-fluoro gluco-configurations and two of them screened for activity against alpha- and beta-gluco-and mannosidase enzymes. Only one substance, the 3-deoxy-3-fluoro-derivative of the gluco-configured tetrahydropyridoimidazole was found to have any activity against a single enzyme, sweet almond beta-glucosidase, and even then at a level 100-fold lower than that of the corresponding simple gluco-configured tetrahydropyridoimidazole thereby underlining the importance of the 3-hydroxy group in the key substrate-enzyme interactions. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.011

文献信息

• Synthesis and evaluation of 3-deoxy and 3-deoxy-3-fluoro derivatives of gluco- and manno-configured tetrahydropyridoimidazole glycosidase inhibitors
  作者：Cécile Ouairy、Thierry Cresteil、Bernard Delpech、David Crich

  DOI：10.1016/j.carres.2013.05.011

  日期：2013.8

  Three tetrahydropyridoimidazole-type glycosidase inhibitors have been synthesized with the 3-deoxy ribo-and arabino-, and 3-deoxy-3-fluoro gluco-configurations and two of them screened for activity against alpha- and beta-gluco-and mannosidase enzymes. Only one substance, the 3-deoxy-3-fluoro-derivative of the gluco-configured tetrahydropyridoimidazole was found to have any activity against a single enzyme, sweet almond beta-glucosidase, and even then at a level 100-fold lower than that of the corresponding simple gluco-configured tetrahydropyridoimidazole thereby underlining the importance of the 3-hydroxy group in the key substrate-enzyme interactions. (c) 2013 Elsevier Ltd. All rights reserved.