3-(6,7-Dimethoxy-1-benzofuran-5-yl)propanoic acid | 1234359-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(6,7-Dimethoxy-1-benzofuran-5-yl)propanoic acid
• CAS: 1234359-09-1
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: ZSUHHOGTXJXTOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-甲氧基补骨脂素 在 ferrous(II) sulfate heptahydrate 、 dipotassium hydrogenphosphate 、 一水合硫酸镁 、 葡萄糖 、 potassium chloride 、 水 、 sodium hydride 、 sodium hydroxide 、 蔗糖 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 171.5h， 生成 3-(6,7-Dimethoxy-1-benzofuran-5-yl)propanoic acid
  参考文献：
  名称：

  Biotransformation of Bergapten and Xanthotoxin by Glomerella cingulata

  摘要：

  The biotransformation of bergapten (1) by the fungus Glomerella cingulata gave the corresponding reduced acid, 6,7-furano-5-methoxy hydrocoumaric acid (2), a new compound. Xanthotoxin (3) was also converted to the corresponding reduced acid cnidiol b (4) and demethylated metabolite xanthotoxol (5) by G. cingulata. The structure of the new compound 2 was elucidated by high-resolution mass spectrometry, extensive NMR techniques, including (1)H NMR and (13)C NMR, (1)H-(1)H correlation spectroscopy, heteronuclear multiple quantum coherence, and heteonuclear multiple bond coherence. The methyl ester or methyl ether or methyl ester and ether derivatives of 2 and 4 were synthesized. All compounds were tested for the beta-secretase (BACE1) inhibitory activity in vitro. The methyl ester and ether derivative 8 was shown to possess BACE1 inhibitory activity, and a IC(50) value was 0.64 +/- 0.04 mM.

  DOI：

  10.1021/jf101064v

文献信息

• Biotransformation of Bergapten and Xanthotoxin by <i>Glomerella cingulata</i>
  作者：Shinsuke Marumoto、Mitsuo Miyazawa

  DOI：10.1021/jf101064v

  日期：2010.7.14

  The biotransformation of bergapten (1) by the fungus Glomerella cingulata gave the corresponding reduced acid, 6,7-furano-5-methoxy hydrocoumaric acid (2), a new compound. Xanthotoxin (3) was also converted to the corresponding reduced acid cnidiol b (4) and demethylated metabolite xanthotoxol (5) by G. cingulata. The structure of the new compound 2 was elucidated by high-resolution mass spectrometry, extensive NMR techniques, including (1)H NMR and (13)C NMR, (1)H-(1)H correlation spectroscopy, heteronuclear multiple quantum coherence, and heteonuclear multiple bond coherence. The methyl ester or methyl ether or methyl ester and ether derivatives of 2 and 4 were synthesized. All compounds were tested for the beta-secretase (BACE1) inhibitory activity in vitro. The methyl ester and ether derivative 8 was shown to possess BACE1 inhibitory activity, and a IC(50) value was 0.64 +/- 0.04 mM.