methyl 5-hydroxy-2-(2-oxopyrrolidin-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate | 1565816-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: methyl 5-hydroxy-2-(2-oxopyrrolidin-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate
• 英文别名: Methyl 5-hydroxy-2-(2-oxopyrrolidin-1-yl)-2,3-dihydrobenzo[g][1]benzofuran-4-carboxylate；methyl 5-hydroxy-2-(2-oxopyrrolidin-1-yl)-2,3-dihydrobenzo[g][1]benzofuran-4-carboxylate
• CAS: 1565816-26-3
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: UXNYPTXLTMQEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,4-二羟基-2-萘甲酸 在 ammonium cerium (IV) nitrate 、 碳酸氢钠 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.33h， 生成 methyl 5-hydroxy-2-(2-oxopyrrolidin-1-yl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate
  参考文献：
  名称：

  Antioxidant and antibacterial evaluation of synthetic furomollugin and its diverse analogs

  摘要：

  Diverse furomollugin (3) and its analogs (11-22) were synthesized in high yields via ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition as a key step. The in vitro antioxidant activities of synthesized compounds were determined by analyzing radical scavenging activities for 1,1-diphenyl-2-picrylhydrazyl (DPPH), nitric oxide, and hydrogen peroxide assays. The results showed that the synthesized furomollugin analogs had effective antioxidant power. Dihydronaphthofurans with 2-alkyoxy or 2-aryl group were the most potent radical scavengers in DPPH assay. Moreover, the antibacterial activities of those compounds were also evaluated and the highly active compounds were selected for further determination of minimal inhibitory concentrations (MICs). Compound 19 (MIC = 2 mu g/mL) was found to be highly active against the gram-negative bacteria Escherichia coli (KCTC-1924) than the Ampicillin standard (MIC = 4 mu g/mL). Compound 22 (MIC = 0.5 mu g/mL) inhibited gram-positive bacteria Staphylococcus aureus (KCTC-1916) growth as effectively as ampicillin (MIC = 0.5 mu g/mL).

  DOI：

  10.1007/s00044-014-0929-9

文献信息

• Antioxidant and antibacterial evaluation of synthetic furomollugin and its diverse analogs
  作者：Likai Xia、Akber Idhayadhulla、Yong Rok Lee、Sung Hong Kim、Young-Jung Wee

  DOI：10.1007/s00044-014-0929-9

  日期：2014.7

  Diverse furomollugin (3) and its analogs (11-22) were synthesized in high yields via ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition as a key step. The in vitro antioxidant activities of synthesized compounds were determined by analyzing radical scavenging activities for 1,1-diphenyl-2-picrylhydrazyl (DPPH), nitric oxide, and hydrogen peroxide assays. The results showed that the synthesized furomollugin analogs had effective antioxidant power. Dihydronaphthofurans with 2-alkyoxy or 2-aryl group were the most potent radical scavengers in DPPH assay. Moreover, the antibacterial activities of those compounds were also evaluated and the highly active compounds were selected for further determination of minimal inhibitory concentrations (MICs). Compound 19 (MIC = 2 mu g/mL) was found to be highly active against the gram-negative bacteria Escherichia coli (KCTC-1924) than the Ampicillin standard (MIC = 4 mu g/mL). Compound 22 (MIC = 0.5 mu g/mL) inhibited gram-positive bacteria Staphylococcus aureus (KCTC-1916) growth as effectively as ampicillin (MIC = 0.5 mu g/mL).