香豆素类席夫碱型Zn~(2+)荧光探针的合成与研究
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摘要
以4-二乙胺基水杨醛和丙二酸二乙酯为原料合成了7-二乙胺基-3-甲酰基香豆素,再与烟酸酰肼反应合成目标产物。在乙腈溶液中,目标产物对Zn~(2+)具有一定的荧光选择性,目标产物与Zn~(2+)的配合比为1∶2。
The target compound-a coumarin Schiff was synthesized through two-step reactions of 4-diethylaminosalicylaldehyde reacting with diethylmalonate to yield 7-diethylamino-coumarin-3-aldehyde,and 7-diethylaminocoumarin-3-aldehyde reacting with nicotinic hydrazide.This novel compound showed very high fluorescent selectivity for Zn~(2+)in acetonitrile,and also experimental data revealed the complex ratio of the title compound and Zn~(2+) to be 1∶ 2.
The target compound-a coumarin Schiff was synthesized through two-step reactions of 4-diethylaminosalicylaldehyde reacting with diethylmalonate to yield 7-diethylamino-coumarin-3-aldehyde,and 7-diethylaminocoumarin-3-aldehyde reacting with nicotinic hydrazide.This novel compound showed very high fluorescent selectivity for Zn~(2+)in acetonitrile,and also experimental data revealed the complex ratio of the title compound and Zn~(2+) to be 1∶ 2.
引文
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[2]FREDERICKSON C J.Neurobiology of zinc and zinc-containing neurons[J].Int.Rev.Neurobiol.,1989,31:145-238.
[3]FREDERICKSON C J,HERNANDEZ M D,MCGINTY J F.Translocation of zinc may contribute to seizure-induced death of neurons[J].Brain Res.,1989,480(1/2):317-321.
[4]CHOI D W,KOH J Y.Zinc and brain injury[J].Annu.Rev.Neurosci.,1998,21:347-375.
[5]BUSH A I.The metallobiology of Alzheimer's disease[J].Trends Neurosci.,2003,26(4):207-214.
[6]HAMBIDGE K M,KREBS N F.Zinc deficiency:a special challenge[J].J.Nutr.,2007,137(4):1 101-1 105.
[7]PRASAD A S.Zinc deficiency[J].Brit.Med.J.,2003,326(7 386):409-410.
[8]AZADBAKHT R,PARVIZ M,TAMARI E,et al.Highly selective fluorescent recognition of Zn2+based on naphthalene macrocyclic derivative[J].Spectrochim.Acta A,2011,82(1):200-204.
[9]马拓,张瑾,刘龙珠,等.Al3+可视化水溶性分子荧光探针的合成及其作用研究[J].有机化学,2014,34(9):1 780-1 785.
[10]DING Yu-bin,LI Xin,LI Tong,et al.α-Monoacylated andα,α'-andα,β'-diacylated dipyrrins as highly sensitive fluorescence turn-on Zn2+probes[J].J.Org.Chem.,2013,78(11):5 328-5 338.
[11]JAFARPOUR F,JALALIMANESH N,OLIA M B A,et al.Silver-catalyzed facile decarbo-xylation of coumarin-3-carboxylic acids[J].Tetrahedron,2010,66(49):9 508-9 511.
[12]WU Jia-sheng,LIU Wei-min,ZHUANG Xiao-qing,et al.Fluorescence turn-on of coumarin derivatives by metal cations:a new signaling mechanism based on CN isomerization[J].Org.Lett.,2007,9(1):33-36.
[13]WU Jia-sheng,SHENG Rui-long,LIU Wei-min,et al.Fluorescent sensors based on controll-able conformational change for discrimination of Zn2+over Cd2+[J].Tetrahedron,2012,68(27/28):5 458-5 463.
[14]KUMAR V,KUMAR A,DIWAN U,et al.A Zn2+-responsive highly sensitive fluorescent probe and 1D coordination polymer based on a coumarin platform[J].Dalton Trans.,2013,42(36):13 078-13 083.