4-amino-5-fluoro-7-ethyl-1-isobutyl-2-[5-(2-bispivaloyloxymethyl-phosphono)furanyl]benzimidazole hydrogenchloride | 1201836-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-amino-5-fluoro-7-ethyl-1-isobutyl-2-[5-(2-bispivaloyloxymethyl-phosphono)furanyl]benzimidazole hydrogenchloride
• 英文别名: [[5-[4-Amino-7-ethyl-5-fluoro-1-(2-methylpropyl)benzimidazol-2-yl]furan-2-yl]-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate;hydrochloride
• CAS: 1201836-57-8
• 化学式: C₂₉H₄₁FN₃O₈P*ClH
• 分子量: 646.093
• InChiKey: DPRWFDULQCZTLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-amino-5-fluoro-7-ethyl-1-isobutyl-2-[5-(2-bispivaloyloxymethyl-phosphono)furanyl]benzimidazole 在 盐酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 0.17h， 以57%的产率得到4-amino-5-fluoro-7-ethyl-1-isobutyl-2-[5-(2-bispivaloyloxymethyl-phosphono)furanyl]benzimidazole hydrogenchloride
  参考文献：
  名称：

  Fructose-1,6-bisphosphatase Inhibitors. 2. Design, Synthesis, and Structure−Activity Relationship of a Series of Phosphonic Acid Containing Benzimidazoles that Function as 5′-Adenosinemonophosphate (AMP) Mimics

  摘要：

  Efforts to enhance the inhibitory potency of the initial purine series of fructose-1,6-bisphosphatase (FBPase) inhibitors led to the discovery of it series of benzirniclazole analogues with hurnan FBPase IC50S < 100 nM. I nhibitor 4.4 emerged as a lead compound based on its potent inhibition of hurnan liver FBPase (IC5() = 55 ilM) and significant glucose lowering in nornial fasted rats. Intravenous administration of 4.4 to Zucker diabetic fatty rats led to rapid and robust glucose lowering, thereby providing the first evidence that FBPase inhibitors could improve glycernia in animal models of type 2 diabetes.

  DOI：

  10.1021/jm901420x