(9aS)-8-acetyl-7-hydroxy-1,3-dimethoxy-N,N,9a-trimethyl-9-oxodibenzofuran-4-carboxamide | 1131540-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (9aS)-8-acetyl-7-hydroxy-1,3-dimethoxy-N,N,9a-trimethyl-9-oxodibenzofuran-4-carboxamide
• CAS: 1131540-83-4
• 化学式: C₂₀H₂₁NO₇
• 分子量: 387.389
• InChiKey: UVQMEBMSVQVGCA-HXUWFJFHSA-N

物化性质

• 沸点：
  649.5±55.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (9aS)-8-乙酰基-1,3,7-三羟基-9a-甲基-9-氧代二苯并呋喃-4-甲酰胺 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以42%的产率得到(9aS)-8-acetyl-7-hydroxy-1,3-dimethoxy-N,N,9a-trimethyl-9-oxodibenzofuran-4-carboxamide
  参考文献：
  名称：

  (−)-Cercosporamide derivatives as novel antihyperglycemic agents

  摘要：

  In our exploratory campaign for an antihyperglycemic agent with a novel mechanism of action, (-)-Cercosporamide 1, which is known as an antifungal agent, showed a potent plasma glucose lowering effect in hyperglycemic KK/Ta mice. The trouble was that it was accompanied by a decrease in food intake and a loss of body weight. We synthesized some (-)-Cercosporamide derivatives and succeeded to separate these actions. N,O-ketal type derivatives, especially compound 10, had the most potent plasma glucose lowering effect without affecting the food consumption or body weight. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.035

文献信息

• (−)-Cercosporamide derivatives as novel antihyperglycemic agents
  作者：Akihiro Furukawa、Tsuyoshi Arita、Susumu Satoh、Kazushi Araki、Masanori Kuroha、Jun Ohsumi

  DOI：10.1016/j.bmcl.2008.12.035

  日期：2009.2

  In our exploratory campaign for an antihyperglycemic agent with a novel mechanism of action, (-)-Cercosporamide 1, which is known as an antifungal agent, showed a potent plasma glucose lowering effect in hyperglycemic KK/Ta mice. The trouble was that it was accompanied by a decrease in food intake and a loss of body weight. We synthesized some (-)-Cercosporamide derivatives and succeeded to separate these actions. N,O-ketal type derivatives, especially compound 10, had the most potent plasma glucose lowering effect without affecting the food consumption or body weight. (C) 2008 Elsevier Ltd. All rights reserved.