(6bS)-8-acetyl-6,9-dihydroxy-3,3,6b-trimethyl-2H-[1]benzofuro[2,3-f][1,3]benzoxazine-1,7-dione | 1131540-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (6bS)-8-acetyl-6,9-dihydroxy-3,3,6b-trimethyl-2H-[1]benzofuro[2,3-f][1,3]benzoxazine-1,7-dione
• CAS: 1131540-85-6
• 化学式: C₁₉H₁₇NO₇
• 分子量: 371.346
• InChiKey: BEYGKRQGRGBMFF-LJQANCHMSA-N

物化性质

• 沸点：
  702.4±60.0 °C(predicted)
• 密度：
  1.56±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：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6bS)-8-acetyl-6,9-dihydroxy-3,3,6b-trimethyl-2H-[1]benzofuro[2,3-f][1,3]benzoxazine-1,7-dione 、 溴甲苯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以79%的产率得到C₃₃H₂₉NO₇
  参考文献：
  名称：

  Discovery of a novel selective PPARγ modulator from (−)-Cercosporamide derivatives

  摘要：

  In an investigation of (-)-Cercosporamide derivatives with a plasma glucose-lowering effect, we found that N-benzylcarboxamide derivative 4 was a partial agonist of PPAR gamma. A SAR study of the substituents on carboxamide nitrogen afforded the N-(1-naphthyl) methylcarboxamide derivative 23 as the most potent selective PPAR gamma modulator. An X-ray crystallography study revealed that compound 23 bounded to the PPAR gamma ligand binding domain in a unique way without any interaction with helix12. Compound 23 displayed a potent plasma glucose-lowering effect in db/db mice without the undesirable increase in body fluid and heart weight that is typically observed when PPAR gamma full agonists are administrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.073
• 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 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以80%的产率得到(6bS)-8-acetyl-6,9-dihydroxy-3,3,6b-trimethyl-2H-[1]benzofuro[2,3-f][1,3]benzoxazine-1,7-dione
  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

• Discovery of a novel selective PPARγ modulator from (−)-Cercosporamide derivatives
  作者：Akihiro Furukawa、Tsuyoshi Arita、Susumu Satoh、Kenji Wakabayashi、Shinko Hayashi、Yumi Matsui、Kazushi Araki、Masanori Kuroha、Jun Ohsumi

  DOI：10.1016/j.bmcl.2010.02.073

  日期：2010.4

  In an investigation of (-)-Cercosporamide derivatives with a plasma glucose-lowering effect, we found that N-benzylcarboxamide derivative 4 was a partial agonist of PPAR gamma. A SAR study of the substituents on carboxamide nitrogen afforded the N-(1-naphthyl) methylcarboxamide derivative 23 as the most potent selective PPAR gamma modulator. An X-ray crystallography study revealed that compound 23 bounded to the PPAR gamma ligand binding domain in a unique way without any interaction with helix12. Compound 23 displayed a potent plasma glucose-lowering effect in db/db mice without the undesirable increase in body fluid and heart weight that is typically observed when PPAR gamma full agonists are administrated. (C) 2010 Elsevier Ltd. All rights reserved.
• (−)-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.