(5R,6R,7S,8S)-2-(2-(biphenyl-4-yl)ethyl)-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol | 1300698-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5R,6R,7S,8S)-2-(2-(biphenyl-4-yl)ethyl)-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
• 英文别名: (5R,6R,7S,8S)-5-(hydroxymethyl)-2-[2-(4-phenylphenyl)ethyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
• CAS: 1300698-44-5
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: XDPKQPFTXHEYSP-MXEMCNAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)-methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 palladium on carbon 、 乙基溴化镁 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、600.01 kPa 条件下， 反应 65.17h， 生成 (5R,6R,7S,8S)-2-(2-(biphenyl-4-yl)ethyl)-5-(hydroxymethyl)-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

文献信息

• Structure–activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors
  作者：Tiehai Li、Lina Guo、Yan Zhang、Jiajia Wang、Zhenxing Zhang、Jing Li、Wenpeng Zhang、Jianping Lin、Wei Zhao、Peng George Wang

  DOI：10.1016/j.bmc.2011.02.043

  日期：2011.4

  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.