8-hydroxy-7-methoxyspiro[3H-chromene-2,1'-cyclopentane]-4-one | 1233078-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-hydroxy-7-methoxyspiro[3H-chromene-2,1'-cyclopentane]-4-one
• CAS: 1233078-29-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: YCGPLULXCOJMLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二羟基-4-甲氧基苯乙酮 、 环戊酮 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 8-hydroxy-7-methoxyspiro[3H-chromene-2,1'-cyclopentane]-4-one
  参考文献：
  名称：

  Antidiabetic and Antiobesity Effects of Ampkinone (6f), a Novel Small Molecule Activator of AMP-Activated Protein Kinase

  摘要：

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.

  DOI：

  10.1021/jm100565d

文献信息

• Antidiabetic and Antiobesity Effects of Ampkinone (<b>6f</b>), a Novel Small Molecule Activator of AMP-Activated Protein Kinase
  作者：Sangmi Oh、Sung Jin Kim、Jung Hwan Hwang、Hyang Yeon Lee、Min Jeong Ryu、Jongmin Park、Soung Jung Kim、Young Suk Jo、Yong Kyung Kim、Chul-Ho Lee、Ki Ryang Kweon、Minho Shong、Seung Bum Park

  DOI：10.1021/jm100565d

  日期：2010.10.28

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.