6-methoxy-3-methyl-2-(2,4,6-trimethoxy-3-(3-methylbut-2-en-1-yl)phenyl)benzofuran | 1253493-05-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 6-methoxy-3-methyl-2-(2,4,6-trimethoxy-3-(3-methylbut-2-en-1-yl)phenyl)benzofuran
• CAS: 1253493-05-8
• 化学式: C₂₄H₂₈O₅
• 分子量: 396.483
• InChiKey: LDPBAASWOUTULJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.06
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-[4,6-dihydroxy-3-(γ,γ-dimethylallyl)-2-methoxyphenyl]-6-hydroxy-3-methyl-benzofuran 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以81%的产率得到6-methoxy-3-methyl-2-(2,4,6-trimethoxy-3-(3-methylbut-2-en-1-yl)phenyl)benzofuran
  参考文献：
  名称：

  Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities

  摘要：

  Two new 2-arylbenzofurans, glycybenzofuran (1) and cyclolicocoumarone (2), together with 10 known flavonoids including licocoumarone (3), glycyrrhisoflavone (4), glisoflavone (5), cycloglycyrrhisoflavone (6), isoliquiritigenin (7), licoflavone A (8), apigenin (9), isokaempferide (10), glycycoumarin (11), and isoglycycoumarin (12), were isolated from the roots of Glycyrrhiza uralensis and their structures were determined by extensive spectroscopic analyses. Compounds 1 and 5 showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity in vitro with the IC50 values of 25.5 and 27.9 mu M, respectively. The structure-activity relationship indicated that the presence of prenyl group and ortho-hydroxy group is important for exhibiting the activity. Kinetic analysis indicated that compound 1 inhibits PTP1B by a competitive mode, whereas compound 5 by a mixed mode. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.110