Methyl 3-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)propanoate | 1072821-76-1

• 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: Methyl 3-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)propanoate
• CAS: 1072821-76-1
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: DVBIRSMIGSDWGI-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

• 作为反应物：
  描述：

  Methyl 3-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)propanoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以15 mg的产率得到5-Methoxypsoralen metabolite X
  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
• 作为产物：
  描述：

  重氮甲烷 、 5-Methoxypsoralen metabolite X 以 丙酮 为溶剂， 以45 mg的产率得到Methyl 3-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)propanoate
  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