6-Hydroxy-7-methoxy-4,4-dimethylchromeno[3,4-e]isoindole-1,3-dione | 1233082-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-Hydroxy-7-methoxy-4,4-dimethylchromeno[3,4-e]isoindole-1,3-dione
• CAS: 1233082-71-7
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: XRFMCUGLCILZHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 6-Hydroxy-7-methoxy-4,4-dimethylchromeno[3,4-e]isoindole-1,3-dione
  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

• Construction of a Polyheterocyclic Benzopyran Library with Diverse Core Skeletons through Diversity-Oriented Synthesis Pathway
  作者：Sangmi Oh、Hwan Jong Jang、Sung Kon Ko、Yeonjin Ko、Seung Bum Park

  DOI：10.1021/cc100044w

  日期：2010.7.12

  In this study, a divergent and practical solid-phase parallel diversity-oriented synthesis (DOS) strategy was successfully applied for the construction of five discrete core skeletons embedded with privileged benzopyranyl substructure. The diversity of these core skeletons was expanded through the introduction of various substituents at the R, R(1), and R(2) positions from a single key intermediate

  在这项研究中，发散和实用的固相平行分集定向合成（DOS）策略已成功地应用于构建五个嵌入有特权苯并吡喃基亚结构的离散核骨架。这些核心骨架的多样性通过在五个不同途径中的单个关键中间体在R，R（1）和R（2）位置处引入各种取代基而得到扩展。更重要的是，我们通过使用库到库的概念，通过核心骨架本身的转换来有效地最大化了分子多样性，并创建了具有相同构件的独特小分子集合。构建了一个434个成员的多杂环苯并吡喃文库，规模约为10 mg，具有进一步多样化的潜力。无需进一步纯化，