937733-19-2Relevant academic research and scientific papers
Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA
Wang, Rui,Liu, Zai-Qun
, p. 1563 - 1569 (2013/07/26)
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, and 2,2′-azobis(2- amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and ?OH-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. Graphical Abstract: Effects on Cu2+/glutathione-, ?OH-, and peroxyl radical-induced oxidation of DNA.[Figure not available: see fulltext.]
Domino ring-opening/recyclization reactions of doubly activated cyclopropanes as a strategy for the synthesis of furoquinoline derivatives
Zhang, Zhiguo,Zhang, Qian,Sun, Shaoguang,Xiong, Tao,Liu, Qun
, p. 1726 - 1729 (2008/02/12)
(Chemical Equation Presented) In one easy step, doubly activated cyclopropanes 1 can be transformed into furoquinoline derivatives 2 through a tandem ring-opening/recyclization reaction mediated by SnCl4·5 H2O. A variety of substrates 1 derived from cheap starting materials were converted into the corresponding furoquinolines in good to excellent yields with high chemo- and regioselectivity. R = H, Me, OMe, Cl, or aromatic group is naphthyl.
