新型荧光假神经递质FFN200的合成方法研究
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摘要
目的:合成新型荧光假神经递质FFN200。方法:3-氨基苯酚的氨基用乙氧羰基进行保护,之后和5-乙酰氨基-3-氧代戊酸乙酯进行Pechmann缩合反应,所得产物用浓盐酸脱保护得荧光假神经递质FFN200。结果:成功合成FFN200。结论:合成方法可行,该方法具有路线短、反应条件温和、产率高,容易操作的特点。
Objective: To synthesize the novel fluorescent false neurotransmitter FFN200. Methods: The amino group of the 3-aminophenol was protected with ethoxycarbonyl,and the produced ethyl( 3-hydroxyphenyl)carbamate was then subjected to condensation with methyl 5-acetamido-3-oxopentanoate via the Pechmann reaction.The prepared product was then deprotected with concentrated hydrochloric acid to give the final product FFN200.Results: FFN200 was successfully synthesized. The synthetic method was workable. Conclusion: This method has the characteristics of short route,mild reaction conditions,high yield,and easy operation.
Objective: To synthesize the novel fluorescent false neurotransmitter FFN200. Methods: The amino group of the 3-aminophenol was protected with ethoxycarbonyl,and the produced ethyl( 3-hydroxyphenyl)carbamate was then subjected to condensation with methyl 5-acetamido-3-oxopentanoate via the Pechmann reaction.The prepared product was then deprotected with concentrated hydrochloric acid to give the final product FFN200.Results: FFN200 was successfully synthesized. The synthetic method was workable. Conclusion: This method has the characteristics of short route,mild reaction conditions,high yield,and easy operation.
引文
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[2]LEE M,GUBERNATOR NG,SULZER D,et al.Development of p H-responsive fluorescent false neurotransmitters[J].J Am Chem Soc,2010,132(26):8828-8830.
[3]PEREIRA DB,SCHMITZ Y,MESZAROS J,et al.Fluorescent false neurotransmitter reveals functionally silent dopamine vesicle clusters in the striatum[J].Nat Neurosci,2016,19(4):578-586.
[4]LIU X,SAVY A,MAURIN S,et al.A dual functional electroactive and fluorescent probe for coupled measurements of vesicular exocytosis with high spatial and temporal resolution[J].Angew Chem Int Ed Engl,2017,56(9):2366-2370.
[5]RAGHUPATHI R,JESSUP CF,LUMSDEN AL,et al.Fusion pore size limits 5-HT release from single enterochromaffin vell vesicles[J].J Cell Physiol,2016,231(7):1593-1600.
[6]LAU T,PROISSL V,ZIEGLER J,et al.Visualization of neurotransmitter uptake and release in serotonergic neurons[J].J Neurosci Methods,2015,241:10-17.
[7]RODRIGUEZ PC,PEREIRA DB,BORGKVIST A,et al.Fluorescent dopamine tracer resolves individual dopaminergic synapses and their activity in the brain[J].Proc Natl Acad Sci USA,2013,110(3):870-875.
[8]ATKINS RL,BLISS DE.Substituted coumarins and azacoumarins.Synthesis and fluorescent properties[J].J Org Chem,1978,43(10):1975-1980.
[9]NATURALE G,LAMBLIN M,COMMANDEUR C,et al.Direct C-H alkylation of naphthoquinones with amino acids through a revisited Kochi-Anderson radical decarboxylation:rrends in reactivity and applications[J].Eur J Org Chem,2012,(30):5774-5788.
[10]DE SK,GRIBBS RA.An efficient and practical procedure for the syntehsis of 4-substituted coumarins[J].Synthesis,2005,8:1231-1233.
[11]周维杰,孙小强,席海涛.含氟香豆素透明质酸衍生物的合成及其荧光性能[J].应用化学,2014,31(8):916-921.
[12]郑华,张光华,相瑞.阳离子香豆素的合成及其对得率浆的返黄抑制作用[J].中国造纸,2015,34(8):13-17.
[13]MOREAU RJ,SORENSEN EJ.Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine[J].Tetrahedron,2007,63:6446-6453.
[14]GUBERNATOR NG,SAMES D,SULZER D,et al.Fluorescent substrates for monoamine transporters as optical false neurotransmitters.US8337941 B2[P].2012-12-25.