6,7-Furano-8a-methoxy-5-prenyloxy hydrocoumaric acid | 1207533-04-7

• 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: 6,7-Furano-8a-methoxy-5-prenyloxy hydrocoumaric acid
• 英文别名: 3-[6-methoxy-4-(3-methylbut-2-enoxy)-1-benzofuran-5-yl]propanoic acid
• CAS: 1207533-04-7
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: ASTLBNTZIYCRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  6,7-Furano-8a-methoxy-5-prenyloxy hydrocoumaric acid methyl ester 在 sodium hydroxide 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以74%的产率得到6,7-Furano-8a-methoxy-5-prenyloxy hydrocoumaric acid
  参考文献：
  名称：

  Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and β-secretase inhibitory activity

  摘要：

  Biotransformation studies conducted on the furanocoumarins isoimperatorin (1) and imperatorin (3) have revealed that 1 was metabolized by Glomerella cingulata to give the corresponding reduced acid, 6,7-furano-5-prenyloxy hydrocoumaric acid (2), and 3 was transformed by G. cingulata to give the dealkylated metabolite, xanthotoxol (4) in high yields (83% and 81%), respectively. The structures of the new compound 2 have been established on the basis of spectral data. The metabolites 2 and 4 were tested for the beta-secretase (BACE1) inhibitory activity in vitro, and metabolite 2 slightly inhibited the beta-secretase activity with an IC50 value of 185.6 +/- 6.8 mu M. The metabolite 4 was less potent activity than compounds 1-3. In addition, methyl ester (2Me), methyl ether (2a) and methyl ester and ether (2aMe) of 2 were synthesized, and investigated for the ability to inhibit beta-secretase. Compound 2aMe exhibited the best beta-secretase inhibitory activity at the IC50 value 16.2 +/- 1.2 mu M and found to be the 2aMe showed competitive mode of inhibition against beta-secretase with K-i value 11.3 +/- 2.8 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.004

文献信息

• Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and β-secretase inhibitory activity
  作者：Shinsuke Marumoto、Mitsuo Miyazawa

  DOI：10.1016/j.bmc.2009.10.004

  日期：2010.1

  Biotransformation studies conducted on the furanocoumarins isoimperatorin (1) and imperatorin (3) have revealed that 1 was metabolized by Glomerella cingulata to give the corresponding reduced acid, 6,7-furano-5-prenyloxy hydrocoumaric acid (2), and 3 was transformed by G. cingulata to give the dealkylated metabolite, xanthotoxol (4) in high yields (83% and 81%), respectively. The structures of the new compound 2 have been established on the basis of spectral data. The metabolites 2 and 4 were tested for the beta-secretase (BACE1) inhibitory activity in vitro, and metabolite 2 slightly inhibited the beta-secretase activity with an IC50 value of 185.6 +/- 6.8 mu M. The metabolite 4 was less potent activity than compounds 1-3. In addition, methyl ester (2Me), methyl ether (2a) and methyl ester and ether (2aMe) of 2 were synthesized, and investigated for the ability to inhibit beta-secretase. Compound 2aMe exhibited the best beta-secretase inhibitory activity at the IC50 value 16.2 +/- 1.2 mu M and found to be the 2aMe showed competitive mode of inhibition against beta-secretase with K-i value 11.3 +/- 2.8 mu M. (C) 2009 Elsevier Ltd. All rights reserved.