(5R,6R,7S,8S)-tris(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine | 263719-95-5

• 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)-tris(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
• 英文别名: (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine；(5R,6R,7S,8S)-2,3-diiodo-6,7,8-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
• CAS: 263719-95-5
• 化学式: C₃₆H₃₄I₂N₂O₄
• 分子量: 812.486
• InChiKey: NCHCECGGCSEUOB-NXVJRICRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 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)-tris(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 乙基溴化镁 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(3,3-dimethylbut-1-ynyl)-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
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1-[(2',2'-dimethoxyethyl)imino]-1,5-imino-D-glucitol 在 N-碘代丁二酰亚胺 、 对甲苯磺酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 (5R,6R,7S,8S)-tris(benzyloxy)-5-[(benzyloxy)methyl]-2,3-diiodo-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

文献信息

• Tight-binding inhibition of jack bean α-mannosidase by glycoimidazole clusters
  作者：Maëva M. Pichon、Fabien Stauffert、Anne Bodlenner、Philippe Compain

  DOI：10.1039/c9ob00826h

  日期：——

  observed in glycosidase inhibition have been achieved so far with jack bean α-mannosidase (JBα-man) using iminosugar clusters based on weakly binding mismatching active-site-directed inhibiting epitopes (inhitopes) in the d-gluco series. Here, we synthesize and evaluate as JBα-man inhibitors a series of mono- to 14-valent glycoimidazoles with inhitopes displaying inhibition values up to the range of

  迄今为止，使用基于亚氨基糖簇的杰克豆α-甘露糖苷酶（JBα-man），已在糖苷酶抑制中观察到了最佳的多价作用，该簇基于d-葡萄糖系列中弱结合错配的活性位点定向抑制性表位（抗原决定簇）。在这里，我们合成并评估了一系列单价至14价的糖咪唑类化合物作为JBα-man抑制剂，其抑制位表现出高达数百nMs的抑制值，以研究抑制位亲和力对多价效应的影响。该系列中最有效的抑制剂是14价的甘露咪唑衍生物，可抑制具有纳摩尔Ki值（2±0.5 nM）的JBα-man，观察到的结合增强至多相对较小（化合价最高可达25倍） -更正的基础）。这项研究的结果支持这样一个事实，即JBα-人-抗体的亲和力和抑制性多价作用的强度向相反的方向发展。发现基于糖基咪唑基的抗原决定基对结合情况的主要影响。多数合成的甘露咪唑簇以及14价的葡萄糖咪唑衍生物被证明是JBα-man的紧密结合抑制剂。
• Very Strong Inhibition of Glucosidases byC(2)-Substituted Tetrahydroimidazopyridines
  作者：Narendra Panday、Yves Canac、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(20000119)83:1<58::aid-hlca58>3.0.co;2-k

  日期：2000.1.19