4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol | 1384974-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol
• 英文别名: 4-Methyl-2,3-dihydrofuro[2,3-b]quinolin-7-ol；4-methyl-2,3-dihydrofuro[2,3-b]quinolin-7-ol
• CAS: 1384974-61-1
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: JIFFBKCJAFXYLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲氧基乙酰乙酰苯胺 在 tin (IV) chloride pentahydrate 、 氢碘酸 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol
  参考文献：
  名称：

  Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA

  摘要：

  The aim of this work was to clarify the influences of the position of hydroxyl group and furo[2,3-b] moiety on the antioxidant effectiveness of quinoline. Thus, 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol (PFQ), 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-8-ol (OFQ), and 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-7-ol (MFQ) were synthesized by a recyclization reaction of 1-acetyl-N-phenylcyclopropanecarboxamide in the presence of SnCl4 as the catalyst. The antioxidant capacities of PFQ, OFQ, and MFQ were evaluated in the experimental system of the oxidation of DNA caused by Cu2+/glutathione (GSH), (OH)-O-aEuro cent, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and (OH)-O-aEuro cent-induced oxidation because the furo[2,3-b] moiety was beneficial for stabilizing the produced furoquinoline radical. Moreover, MFQ can decrease the oxidation rate of AAPH-induced oxidation of DNA, while PFQ and OFQ can inhibit AAPH-induced oxidation of DNA for a period. The data obtained from AAPH-induced oxidation of DNA were treated by chemical kinetic method; it was found that PFQ and OFQ can trap 1.3 and 1.5 radicals, respectively. Therefore, the hydroxyl group at different positions changed the mechanism of furoquinoline in protecting DNA against radical-induced oxidation.Effects on Cu2+/glutathione-, (OH)-O-aEuro cent-, and peroxyl radical-induced oxidation of DNA.

  DOI：

  10.1007/s00044-012-0157-0

文献信息

• Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA
  作者：Rui Wang、Zai-Qun Liu

  DOI：10.1007/s00044-012-0157-0

  日期：2013.4

  The aim of this work was to clarify the influences of the position of hydroxyl group and furo[2,3-b] moiety on the antioxidant effectiveness of quinoline. Thus, 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol (PFQ), 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-8-ol (OFQ), and 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-7-ol (MFQ) were synthesized by a recyclization reaction of 1-acetyl-N-phenylcyclopropanecarboxamide in the presence of SnCl4 as the catalyst. The antioxidant capacities of PFQ, OFQ, and MFQ were evaluated in the experimental system of the oxidation of DNA caused by Cu2+/glutathione (GSH), (OH)-O-aEuro cent, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and (OH)-O-aEuro cent-induced oxidation because the furo[2,3-b] moiety was beneficial for stabilizing the produced furoquinoline radical. Moreover, MFQ can decrease the oxidation rate of AAPH-induced oxidation of DNA, while PFQ and OFQ can inhibit AAPH-induced oxidation of DNA for a period. The data obtained from AAPH-induced oxidation of DNA were treated by chemical kinetic method; it was found that PFQ and OFQ can trap 1.3 and 1.5 radicals, respectively. Therefore, the hydroxyl group at different positions changed the mechanism of furoquinoline in protecting DNA against radical-induced oxidation.Effects on Cu2+/glutathione-, (OH)-O-aEuro cent-, and peroxyl radical-induced oxidation of DNA.