典型文献
CuBr-promoted domino Biginelli reaction for the diastereoselective synthesis of bridged polyheterocycles:Mechanism studies and in vitro anti-tumor activities
文献摘要：
The low-cost CuBr-promoted domino Biginelli reaction among readily available ketones,salicylalde-hyde derivatives and 3-amino-l,2,4-triazole was studied under solvothermal conditions,giving the novel bridged polyheterocycles bearing two or three stereocenters depending on the starting ketones.This mul-ticomponent reaction proceeded with high diastereoselectivity(dr＞20∶1)based on a combined 1H NMR,crystallographic and supercritical fluid chromatographic(SFC)analysis of the product.Time-dependent high-resolution mass spectrometry(HRMS)was performed to track the reaction process,and several key intermediates were identified,leading to the drawing of a plausible reaction mechanism.Density func-tional theory(DFT)calculation was supplemented,and two reaction pathways were differentiated.More-over,in vitro antitumor activity was evaluated using HeLa and HepG2 cell lines,and two of these poly-heterocycles demonstrated promising activities against HepG2 cells with EC50 down to 10 μmol/L.Addi-tionally,ESI-MS/MS studies on all the polyheterocycles suggest a common fragmentation pathway(loss of one molecule of amino-triazole)they shared,providing the first-hand fragmentation rules for future rapid structural identification of them.The multicomponent domino reaction presented here may offer prospects for future design of more efficient strategies to access medicinally important bridged polyhete-rocycles.
文献关键词：
中图分类号：
作者姓名：
Mengting Zeng;Ying Xue;Yunan Qin;Fen Peng;Quan Li;Ming-Hua Zeng
作者机构：
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials,Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules,College of Chemistry and Chemical Engineering,Hubei University,Wuhan 430062,China;Sichuan Center for Disease Control and Prevention,Chengdu 610041,China;Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources,School of Chemistry and Pharmaceutical Sciences,Guangxi Normal University,Guilin 541004,China
文献出处：
引用格式：
[1]Mengting Zeng;Ying Xue;Yunan Qin;Fen Peng;Quan Li;Ming-Hua Zeng-.CuBr-promoted domino Biginelli reaction for the diastereoselective synthesis of bridged polyheterocycles:Mechanism studies and in vitro anti-tumor activities)[J].中国化学快报（英文版）,2022(11):4891-4895
A类：
diastereoselective,polyheterocycles,salicylalde,stereocenters,ticomponent,polyhete,rocycles
B类：
CuBr,promoted,domino,Biginelli,reaction,synthesis,bridged,Mechanism,studies,vitro,activities,low,cost,among,readily,available,ketones,hyde,derivatives,amino,triazole,was,studied,under,solvothermal,conditions,giving,novel,bearing,two,three,depending,starting,This,proceeded,high,diastereoselectivity,combined,1H,NMR,crystallographic,supercritical,fluid,chromatographic,SFC,analysis,product,Time,dependent,resolution,mass,spectrometry,HRMS,performed,track,process,several,key,intermediates,were,identified,leading,drawing,plausible,mechanism,Density,func,theory,DFT,calculation,supplemented,pathways,differentiated,More,over,antitumor,activity,evaluated,using,HeLa,HepG2,lines,these,demonstrated,promising,against,cells,EC50,down,Addi,tionally,ESI,suggest,common,fragmentation,loss,molecule,they,shared,providing,first,hand,rules,future,rapid,structural,identification,them,multicomponent,presented,here,may,offer,prospects,design,more,efficient,strategies,access,medicinally,important
AB值：
0.605196
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