N-ethyl-N-[(5-[4-(ethylsulfonyl)phenoxy]-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-6-yl)methyl]acetamide | 1193347-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-ethyl-N-[(5-[4-(ethylsulfonyl)phenoxy]-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-6-yl)methyl]acetamide
• CAS: 1193347-12-4
• 化学式: C₃₁H₄₀N₄O₅SSi
• 分子量: 608.834
• InChiKey: LHDOSVZMGVOZOE-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-[(5-[4-(ethylsulfonyl)phenoxy]-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-6-yl)methyl]acetamide 在 三氟乙酸 、 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 以12.5 mg的产率得到N-ethyl-N-({5-[4-(ethylsulfonyl)phenoxy]-2-(pyridin-2-yl)-1H-benzimidazol-6-yl}methyl)acetamide
  参考文献：
  名称：

  The design and optimization of a series of 2-(pyridin-2-yl)-1H-benzimidazole compounds as allosteric glucokinase activators

  摘要：

  The optimization of a series of benzimidazole glucokinase activators is described. We identified a novel and potent achiral benzimidazole derivative as an allosteric GK activator. This activator was designed and synthesized via removal of the chiral center of the lead compound, 6-(N-acylpyrrolidin-2-yl)benzimidazole. The activator exhibited good PK profiles in rats and dogs, and significant hypoglycemic efficacy at 1 mg/kg po dosing in a rat OGTT model. The binding site and binding mode of the benzimidazole class of GKA with GK protein was confirmed by X-ray crystallographic analysis. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.037
• 作为产物：
  描述：

  N-[(5-[4-(ethylsulfonyl)phenoxy]-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-6-yl)methyl]acetamide 、 碘乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 2.0h， 生成 N-ethyl-N-[(5-[4-(ethylsulfonyl)phenoxy]-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-6-yl)methyl]acetamide
  参考文献：
  名称：

  The design and optimization of a series of 2-(pyridin-2-yl)-1H-benzimidazole compounds as allosteric glucokinase activators

  摘要：

  The optimization of a series of benzimidazole glucokinase activators is described. We identified a novel and potent achiral benzimidazole derivative as an allosteric GK activator. This activator was designed and synthesized via removal of the chiral center of the lead compound, 6-(N-acylpyrrolidin-2-yl)benzimidazole. The activator exhibited good PK profiles in rats and dogs, and significant hypoglycemic efficacy at 1 mg/kg po dosing in a rat OGTT model. The binding site and binding mode of the benzimidazole class of GKA with GK protein was confirmed by X-ray crystallographic analysis. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.037