2-(4-((3-morpholinopropyl)amino)quinazolin-2-yl)-1H-indole-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(4-((3-morpholinopropyl)amino)quinazolin-2-yl)-1H-indole-3-carbaldehyde
• 英文别名: 2-[4-(3-morpholin-4-ylpropylamino)quinazolin-2-yl]-1H-indole-3-carbaldehyde
• 化学式: C₂₄H₂₅N₅O₂
• 分子量: 415.495
• InChiKey: AWYRMJOBOADMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  bouchardatine 在 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 2-(4-((3-morpholinopropyl)amino)quinazolin-2-yl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Bouchardatine Derivatives as Potential Adipogenesis/Lipogenesis Inhibitors for Antiobesity Treatment

  摘要：

  Our recent study has shown that the natural product bouchardatine (1) can reduce the triglyceride (TG) content in 3T3-L1 adipocytes (EC50 approximate to 25 mu M). Here, we synthesized two series of compounds by introducing amine side chains at the 5 or 8 position of 1 and evaluated the lipid-lowering activity of derivatives. It was found that some of the compounds had significant lipid-lowering effects, and the most active compound 3d showed better activity (EC50 = 0.017 mu M) than 2 (EC50 = 0.086 mu M), a compound reported by us. Further, the mechanism studies revealed that 3d blocked TG accumulation via activation of the LKB1-AMPK signaling pathway, efficiently down-regulating the expression of key regulators of adipogenesis/lipogenesis. Cell uptake assay and confocal imaging of 3d in cells indicated that compound 3d had favorable cell permeability. Our results suggest that 3d may be a promising agent for the treatment of obesity and related metabolic disorders.

  DOI：

  10.1021/acs.jmedchem.5b01566