[2,2-dimethylpropanoyloxymethoxy-[5-(5-oxo-4H-1,2-oxazol-3-yl)furan-2-yl]phosphoryl]oxymethyl 2,2-dimethylpropanoate | 1243184-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2,2-dimethylpropanoyloxymethoxy-[5-(5-oxo-4H-1,2-oxazol-3-yl)furan-2-yl]phosphoryl]oxymethyl 2,2-dimethylpropanoate
• CAS: 1243184-61-3
• 化学式: C₁₉H₂₆NO₁₀P
• 分子量: 459.39
• InChiKey: LAOJXPPOVGDZFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (((5-formylfuran-2-yl)phosphoryl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate) 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [2,2-dimethylpropanoyloxymethoxy-[5-(5-oxo-4H-1,2-oxazol-3-yl)furan-2-yl]phosphoryl]oxymethyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  A Potent and Selective AMPK Activator That Inhibits de Novo Lipogenesis

  摘要：

  AMP-activated protein kinase (AMPK) is a heterotrimeric kinase that regulates cellular. energy metabolism by affecting energy-consuming pathways such as de novo. lipid biosynthesis and glucose production as well as energy-producing pathways such as lipid oxidation and glucose uptake. Accordingly, compounds that activate AMPK represent potential drug candidates for the treatment of hyperlipidemia and type 2 diabetes. Screening of a proprietary library of AMP mimetics identified the phosphonic acid 2 that bears little structural resemblance to AMP but is capable of activating AMPK with high potency (EC(50) = 6 nM vs AMP EC(50) = 6 mu M) and specificity. Phosphonate prodrugs of 2 inhibited de novo lipogenesis In cellular and animal models of hyperlipidemia.

  DOI：

  10.1021/ml100143q

文献信息

• A Potent and Selective AMPK Activator That Inhibits de Novo Lipogenesis
  作者：Jorge E. Gómez-Galeno、Qun Dang、Thanh H. Nguyen、Serge H. Boyer、Matthew P. Grote、Zhili Sun、Mingwei Chen、William A. Craigo、Paul D. van Poelje、Deidre A. MacKenna、Edward E. Cable、Paul A. Rolzin、Patricia D. Finn、Bert Chi、David L. Linemeyer、Scott J. Hecker、Mark D. Erion

  DOI：10.1021/ml100143q

  日期：2010.12.9

  AMP-activated protein kinase (AMPK) is a heterotrimeric kinase that regulates cellular. energy metabolism by affecting energy-consuming pathways such as de novo. lipid biosynthesis and glucose production as well as energy-producing pathways such as lipid oxidation and glucose uptake. Accordingly, compounds that activate AMPK represent potential drug candidates for the treatment of hyperlipidemia and type 2 diabetes. Screening of a proprietary library of AMP mimetics identified the phosphonic acid 2 that bears little structural resemblance to AMP but is capable of activating AMPK with high potency (EC(50) = 6 nM vs AMP EC(50) = 6 mu M) and specificity. Phosphonate prodrugs of 2 inhibited de novo lipogenesis In cellular and animal models of hyperlipidemia.