2-(2',4'-Dimethoxyphenyl)-4,6-dimethoxy-5-(γ,γ-dimethylallyl)-coumaron | 66056-43-7

• 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: 2-(2',4'-Dimethoxyphenyl)-4,6-dimethoxy-5-(γ,γ-dimethylallyl)-coumaron
• 英文别名: Licocoumarone trimethylether；2-(2,4-dimethoxy-phenyl)-4,6-dimethoxy-5-(3-methyl-but-2-enyl)-benzofuran；2-(2,4-dimethoxyphenyl)-4,6-dimethoxy-5-(3-methylbut-2-enyl)-1-benzofuran
• CAS: 66056-43-7
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: CQQBYXRTSPRZOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[6-羟基-4-甲氧基-5-(3-甲基丁-2-烯-1-基)-1-苯并呋喃-2-基]苯-1,3-二酚 、 重氮甲烷 生成 2-(2',4'-Dimethoxyphenyl)-4,6-dimethoxy-5-(γ,γ-dimethylallyl)-coumaron
  参考文献：
  名称：

  甘草的抗氧化剂和抗菌成分：一种新的苯并呋喃衍生物的分离和结构解析。

  摘要：

  A new 2-arylbenzofuran derivative named licocoumarone (IIa) was isolated from commercially available xibei licorice (seihoku kanzo) along with a known 3-arylcoumarin derivative, glycycoumarin (Ia), and the structure of IIa was elucidated as 2-(2, 4-dihydroxyphenyl)-6-hydroxy-4-methoxy-5-(3-methyl-2-butenyl)coumarone on the basis of spectroscopic and chemical studies. Both Ia and IIa exhibited antimicrobial activities, whereas only IIa had antioxidant activity.

  DOI：

  10.1248/cpb.36.3474

文献信息

• Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities
  作者：Songpei Li、Wei Li、Yinghua Wang、Yoshihisa Asada、Kazuo Koike

  DOI：10.1016/j.bmcl.2010.07.110

  日期：2010.9

  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.
• DEMIZU, SACHIO;KAJIYAMA, KIICHIRO;TAKAHASHI, KUNIO;HIRAGA, YUKIO;YAMAMOTO+, CHEM. AND PHARM. BULL., 36,(1988) N 9, C. 3474-3479
  作者：DEMIZU, SACHIO、KAJIYAMA, KIICHIRO、TAKAHASHI, KUNIO、HIRAGA, YUKIO、YAMAMOTO+

  DOI：——

  日期：——