(E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-phenethylbenzoate | 1422251-65-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-phenethylbenzoate
• 英文别名: amorfrutin B methyl ester；methyl 3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2-hydroxy-4-methoxy-6-(2-phenylethyl)benzoate
• CAS: 1422251-65-7
• 化学式: C₂₇H₃₄O₄
• 分子量: 422.565
• InChiKey: CMSPFJHCVZUTPP-XSFVSMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-phenethylbenzoate 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 以70%的产率得到amorfrutin B
  参考文献：
  名称：

  Structural Characterization of Amorfrutins Bound to the Peroxisome Proliferator-Activated Receptor γ

  摘要：

  Amorfrutins are a family of natural products with high affinity to the peroxisome proliferator-activated receptor gamma (PPAR gamma), a nuclear receptor regulating lipid and glucose metabolism. The PPAR gamma agonist rosiglitazone increases insulin sensitivity and is effective against type II diabetes but has severe adverse effects including weight gain. Amorfrutins improve insulin sensitivity and dyslipidemia but do not enhance undesired fat storage. They bear potential as therapeutics or prophylactic dietary supplements. We identified amorfrutin B as a novel partial agonist of PPAR gamma with a considerably higher affinity than that of previously reported amorfrutins, similar to that of rosiglitazone. Crystal structures reveal the geranyl side chain of amorfrutin B as the cause of its particularly high affinity. Typical for partial agonists, amorfrutins 1, 2, and B bind helix H3 and the beta-sheet of PPARy gamma but not helix H12.

  DOI：

  10.1021/jm3013272
• 作为产物：
  描述：

  methyl 2-hydroxy-4-methoxy-6-phenethylbenzoate 、 香叶基氯 在 potassium hydride 作用下， 以 甲苯 为溶剂， 反应 2.67h， 以45%的产率得到(E)-methyl 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-phenethylbenzoate
  参考文献：
  名称：

  Structural Characterization of Amorfrutins Bound to the Peroxisome Proliferator-Activated Receptor γ

  摘要：

  Amorfrutins are a family of natural products with high affinity to the peroxisome proliferator-activated receptor gamma (PPAR gamma), a nuclear receptor regulating lipid and glucose metabolism. The PPAR gamma agonist rosiglitazone increases insulin sensitivity and is effective against type II diabetes but has severe adverse effects including weight gain. Amorfrutins improve insulin sensitivity and dyslipidemia but do not enhance undesired fat storage. They bear potential as therapeutics or prophylactic dietary supplements. We identified amorfrutin B as a novel partial agonist of PPAR gamma with a considerably higher affinity than that of previously reported amorfrutins, similar to that of rosiglitazone. Crystal structures reveal the geranyl side chain of amorfrutin B as the cause of its particularly high affinity. Typical for partial agonists, amorfrutins 1, 2, and B bind helix H3 and the beta-sheet of PPARy gamma but not helix H12.

  DOI：

  10.1021/jm3013272

文献信息

• Structural Characterization of Amorfrutins Bound to the Peroxisome Proliferator-Activated Receptor γ
  作者：Jens C. de Groot、Christopher Weidner、Joern Krausze、Ken Kawamoto、Frank C. Schroeder、Sascha Sauer、Konrad Büssow

  DOI：10.1021/jm3013272

  日期：2013.2.28

  Amorfrutins are a family of natural products with high affinity to the peroxisome proliferator-activated receptor gamma (PPAR gamma), a nuclear receptor regulating lipid and glucose metabolism. The PPAR gamma agonist rosiglitazone increases insulin sensitivity and is effective against type II diabetes but has severe adverse effects including weight gain. Amorfrutins improve insulin sensitivity and dyslipidemia but do not enhance undesired fat storage. They bear potential as therapeutics or prophylactic dietary supplements. We identified amorfrutin B as a novel partial agonist of PPAR gamma with a considerably higher affinity than that of previously reported amorfrutins, similar to that of rosiglitazone. Crystal structures reveal the geranyl side chain of amorfrutin B as the cause of its particularly high affinity. Typical for partial agonists, amorfrutins 1, 2, and B bind helix H3 and the beta-sheet of PPARy gamma but not helix H12.