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Green Synthesis and Catalysis 2023年第4期4卷 321-329页

作者： Xinling Cao Yinggang Duan Kaihong Lv Zihan Lu Yihua Chen Shengjiao Yan Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University) Ministry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming 650091China

A novel protocol for the preparation of highly functionalized 2-azabicyclo[3.3.1]nonane(morphan)derivatives via a multicomponent cascade reaction,involving 3-formylchromones,2-naphthols,and enaminones in the ionic liquid[BMIM]PF6 as the solvent and promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU),was developed,which involved the cleavage of one C–O bond and formation of four bonds(1 C–O,1 C–N,and 2 C–C bonds).As a result,a series of morphan derivatives were produced through a cascade reaction,including a sequence of 1,2-addition,enol-keto tautomerization,Michael addition,dehydration,another Michael addition,imine-enamine tautomerization,and N-alkylation reactions,which were accompanied by a ring-opening reaction.This protocol was suitable for combinatorial and parallel syntheses of natural product-like morphan compounds in a one-pot reaction rather than through tedious multi-step reactions.

关键词： Morphan derivatives Site-selective synthesis cascade reaction Enaminones 3-Formylchromones

Multicomponent cascade reaction of 3-formylchromones:Highly regioselective synthesis of functionalized pyridin-2(1H)-ones

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绿色合成与催化(英文)

绿色合成与催化(英文) 2023年第3期4卷 231-239页

作者： Xinghan Yun Li Chen Ying Lv Zihan Lu Kun Huang Shengjiao Yan Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University) Ministry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming650091China

A novel protocol was developed for the construction of highly functionalized pyridin-2(1H)-ones from 3-formylchromones,ethyl 2-(pyridin-2-yl)acetate derivatives and amines via a complex multicomponent cascade reaction involving targeted duplicated ring-opening and duplicated cyclization reactions which form skeleton-reorganized target compounds.A series of pyridin-2(1H)-ones were produced by this reaction accompanied by the formation of three bonds(one C–N and two C–C bonds)and the cleavage of one bond in one step.This protocol can be used in combinatorial and parallel syntheses of various pyridin-2(1H)-ones with potent biological activity.The advantages of this approach include simple and practical operation(multicomponent one-pot),high yields(up to 91%),and products with potential biological activity.

关键词： Pyridin-2(1H)-ones cascade reaction Selective synthesis 3-Formylchromones

cascade reaction-based fluorescent probe for detection of H2S with the assistance of CTAB micelles

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Chinese Chemical Letters 2016年第12期27卷 1793-1796页

作者： Hai-Rong Zheng Li-Ya Niu Yu-Zhe Chen Li-Zhu Wu Chen-Ho Tung Qing-Zheng Yang Technical Institute of Physics and Chemistry Chinese Academy of Sciences Beijing 100190 China College of Chemistry Beijing Normal University Beijing 100875 China University of the Chinese Academy of Sciences Beijing 100049 China

We report a turn-on fluorescent probe for H2S through a cascade reaction using a new trap group 4- （bromomethyl）benzoate, based on excited-state intramolecular proton transfer （ESIPT） sensing mechanism. The probe showed good selectivity and high sensitivity towards H2S and it was capable of detecting and imaging H2S in living HeLa cells, indicating its potential biological applications.

关键词： Hydrogen sulfide Fluorescent probe cascade reaction ESIPT Micelles

Pd@Ir-LOD multienzyme utilizing endogenous lactate consumption cooperates with photothermal for tumor therapy

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Nano Research 2024年第1期17卷 270-281页

作者： Zichen Ye Yun Li Jingchao Li Xinyan Hu Jinyang Zheng Gongxin Zhang Sijin Xiang Tianbao Zhu Zhide Guo Xiaolan Chen State Key Laboratory for Physical Chemistry of Solid Surfaces Collaborative Innovation Center of Chemistry for Energy Materials and Engineering Research Center for Nano-Preparation Technology of Fujian ProvinceCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China State Key Laboratory of Molecular Vaccinology and Molecular Diagnostics&Center for Molecular Imaging and Translational Medicine School of Public Health Xiamen UniversityXiamen 361102China The High Educational Key Laboratory for Biomedical Engineering&Key Laboratory of Fire Retardant Materials of Fujian Province Department of BiomaterialsCollege of MaterialsXiamen UniversityXiamen 361102China

Lactic acid(LA)plays a major role in the occurrence,development,and spread of cancer.Enlightened by its high accumulation in tumor site,a novel lactate oxidase(LOD)conjugated two-dimensional Pd@Ir nanoplatform(Pd@Ir-LOD,PIL)was fabricated to combine cascade reaction with photothermal for tumor therapy.In detail,the overexpressed LA in tumor microenvironment(TME)was a key factor to activate the PIL-based cascade reaction:(1)Plenty of H_(2)O_(2)could be generated from LA by the catalysis of LOD with O_(2);(2)potent·OH was produced from H_(2)O_(2)due to the peroxidase(POD)-like activity of PIL;(3)meantime,PIL’s catalase(CAT)-like activity could decompose part H_(2)O_(2)into O_(2)to achieve the purpose of LA cyclic oxidization.Moreover,the reduced glutathione(GSH)scavenging capability of PIL might protect the produced reactive oxygen species(ROS)from being cleared to further improve the cascade therapeutic effect.More importantly,PIL had excellent photothermal conversion efficiency(37.35%)and manifested a surprising temperature rising effect in tumor.Taken together,the decreasing LA concentration,accumulation of high-toxic ROS,the depletion of GSH together with the higher intra-tumoral temperature potently enhanced in vivo antitumor therapy.Therefore,a promising therapeutic tactic based on PIL integrating endogenous LA consumption,chemodynamic therapy(CDT),and photothermal therapy(PTT)has been put forward.

关键词： lactate oxidase chemodynamic therapy photothermal therapy cascade reaction tumor microenvironment

Stereodivergent synthesis ofα-fluoroα-azaarylγ-butyrolactones via cooperative copper and iridium catalysis

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Fundamental Research 2024年第1期4卷 77-85页

作者： Kui Tian Xin Chang Lu Xiao Xiu-Qin Dong Chun-Jiang Wang College of Chemistry and Molecular Sciences Engineering Research Center of Organosilicon Compounds&MaterialsMinistry of EducationWuhan UniversityWuhan 430072China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryShanghai 230021China Suzhou Institute of Wuhan University Suzhou 215123China

The development of stereodivergent synthetic methods to access all four stereoisomers of biologically importantα-fluoroγ-butyrolactones containing vicinal stereocenters is of great importance and poses a formidable challenge owing to ring strain and steric hindrance.Herein,a novel asymmetric[3+2]annulation ofα-fluoroα-azaaryl acetates with vinylethylene carbonate was successfully developed through Cu/Ir-catalyzed cascade allylic alkylation/lactonization,affording a variety of enantioenrichedα-fluoroγ-butyrolactones bearing vicinal stereogenic centers with high reaction efficiency and excellent levels of both stereoselectivity and regioselectivity(up to 98%yield,generally>20:1 dr and>99%ee).Notably,all four stereoisomers of these pharmaceutically valuable molecules could be accessed individually via simple permutations of two enantiomeric catalysts.In addition,other azaaryl acetates bearingα-methyl,α-chlorine orα-phenyl group were tolerated well in this transformation.reaction mechanistic investigations were conducted to explore the process of this bimetallic catalysis based on the results of reaction intermediates,isotopic labelling experiments,and kinetic studies.

关键词： Asymmetric catalysis α-Fluoroγ-butyrolactones Synergistic catalysis cascade reaction Stereodivergent synthesis

Positional assembly of multi-enzyme cascade reaction in polyelectrolyte doped microcapsule through electrospray and layer-by-layer assembly

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Synthetic and Systems Biotechnology 2020年第3期5卷 206-213页

作者： Shiyi Che Jie Wang Xiaoyuan Ji Zhiguo Su Shaomin Wang Songping Zhang State Key Laboratory of Biochemical Engineering Institute of Process EngineeringChinese Academy of SciencesBeijing100190China University of Chinese Academy of Sciences No.19 Yuquan RoadShijingshan DistrictBeijing100049China College of Chemistry Zhengzhou UniversityZhengzhou450001China

Polyelectrolyte-doped microcapsules(PDM)was fabricated by coaxial electrospray of a mixture of glycerol and water containing 10 mg/mL cationic polyelectrolyte poly(allylamine hydrochloride)(PAH)fed as the core phase solution,and a N,N-dimethylacetylamide solution of 10 wt%polyurethane fed as the shell phase solution.Multienzyme system involving Candida Antarctica lipase B(CALB),glucose oxidase(GOD),and horseradish peroxidase(HRP)for cascade reaction was assembled in the PDM at three different places,namely,surface,shell,and lumen.Placing of enzyme inside aqueous lumen of the PDM was realized by in situ encapsulation through adding the enzyme in the core-phase solution for coaxial electrospray.By ion-pairing of enzyme with cationic surfactant CTAB,an organic soluble enzyme-CTAB complex was prepared,so that in situ embedding of enzyme in the shell of the PDM was realized by adding it into the shell phase solution.Surface attachment of enzymes was achieved by layer-by-layer(LbL)technology,which is based on the ion-exchange interactions between oppositely charged enzymes and PAH that was doped in PDM.The enzyme-decorated microcapsule was then studied as a microbioreactor,in which 1-Oxododecyla-α-glucopyranoside was converted by CALB to glucose,which was oxidised by GOD to gluconolactone in a second step.The hydrogen peroxide produced was then used by HRP to oxidize ABTS to form coloured radical cation ABTS•+for activity analysis.The successful fabrication of the PDM and precise localization of enzymes in the PDM by different strategies were fully characterized.By varying the immobilization strategy,totally six PDM bioreactors with three enzymes precisely positional assembled in different strategies were constructed and their activities for the cascade reaction were investigated and compared.The PDM micro-bioreactor prepared by novel electrospray technologies provide a smart platform for positional assembly of multi-enzyme cascade reaction in a precise and well-controlled manner.

关键词： Coaxial electrospray Microcapsule Multi-enzyme cascade reaction Positional assembly Layer-by-layer assembly

NIR-II driven plasmon-enhanced cascade reaction for tumor microenvironment-regulated catalytic therapy based on bio-breakable Au-Ag nanozyme

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Nano Research 2020年第8期13卷 2118-2129页

作者： Min Xu Qianglan Lu Yiling Song Lifang Yang Chuchu Ren Wen Li Ping Liu Yule Wang Yan Zhu Nan Li Tianjin Key Laboratory of Drug Delivery&High-Efficiency School of Pharmaceutical Science and TechnologyTianjin UniversityTianjin300072China Tianjin State Key Laboratory of Modern Chinese Medicine Tianjin University of Traditional Chinese MedicineTianjin301617China Research and Development Center of TCM Tianjin International Joint Academy of Biotechnology and MedicineTianjin300457China

Emerging nanozymes with natural enzyme-mimicking catalytic activities have inspired extensive research interests due to their high stability,low cost,and simple preparation,especially in the field of catalytic tumor therapy.Here,bio-breakable nanozymes based on glucose-oxidase(GOx)-loaded biomimetic Au–Ag hollow nanotriangles(Au–Ag–GOx HTNs)are designed,and they trigger an near-infrared(NIR)-II-driven plasmon-enhanced cascade catalytic reaction through regulating tumor microenvironment(TME)for highly efficient tumor therapy.Firstly,GOx can effectively trigger the generation of gluconic acid(H+)and hydrogen peroxide(H2O2),thus depleting nutrients in the tumor cells as well as modifying TME to provide conditions for subsequent peroxidase(POD)-like activity.Secondly,NIR-II induced surface plasmon resonance can induce hot electrons to enhance the catalytic activity of Au–Ag–GOx HTNs,eventually boosting the generation of hydroxyl radicals(•OH).Interestingly,the generated H2O2 and H+can simultaneously induce the degradation of Ag nanoprisms to break the intact triangle nanostructure,thus promoting the excretion of Au–Ag–GOx HTNs to avoid the potential risks of drug metabolism.Overall,the NIR-II driven plasmon-enhanced catalytic mechanism of this bio-breakable nanozyme provides a promising approach for the development of nanozymes in tumor therapy.

关键词： near-infrared(NIR)-II driven plasmon-enhanced catalysis Au-Ag hollow nan otria ngles bio-breakable cascade reaction

4-Dimethylaminopyridine-catalyzed cascade reaction for Efficient Synthesis of Naphthofurans

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Chemical Research in Chinese Universities 2016年第1期32卷 62-67页

作者： FAN Chenli HE Xinwei LIAO Kaisheng WANG Cui'e SHANG Yongjia Department of Material Engineering Wuhu Institute of Technology Wuhu 241003 P. R. China Key Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Molecule-based Materials College of Chemistry and Materials Science Anhui Normal University Wuhu 241000 P. R. China

A convenient and efficient method was developed for the synthesis of naphtho[2,1-blfurans via 4-dimethylaminopyridine（DMAP）-catalyzed cascade reaction of 2-hydroxy-l-naphthaldehydes and a-halogenated ketones in moderate to good yields in the presence of Na2CO3 at 80 ~C for 6 h. The mechanism for this process was briefly discussed with a tentative catalytic cycle proposed. Moreover, this method features organocatalysts and high step-economy, which makes it practical and attractive.

关键词： 4-Dimethylaminopyridine a-Halogenated ketone cascade reaction Naphthofuran Organocatalysis

NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles

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Chinese Chemical Letters 2021年第8期32卷 2567-2571页

作者： Haijun Leng Qian Zhao Qing Mao Shuaijiang Liu Menglan Luo Rui Qin Wei Huang Gu Zhan State Key Laboratory of Southwestern Chinese Medicine Resources School of Pharmacy and School of Basic Medical SciencesChengdu University of Traditional Chinese MedicineChengdu 611137China Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province Sichuan Industrial Institute of AntibioticsSchool of PharmacyChengdu UniversityChengdu 610052China

An N-heterocyclic carbene(NHC)-catalysed retro-aldol/aldol cascade reaction of spirooxindole-basedβ-hydroxyaldehyde has been developed.The ring opening-closure process enables the diastereodivergent synthesis of spirocyclopentaneoxindole products with four consecutive stereocenters by simply changing the reaction solvents(THF or DCE).The Michael/aldol/retro-aldol/aldol sequential protocol allows the diastereodivergent synthesis of spirocyclopentaneoxindoles from 3-substituted oxindole andα,β-unsaturated aldehyde under the relay catalysis of a chiral secondary amine and an NHC catalyst.Moreover,four stereoisomers of the product can be selectively provided by using different combinations of a chiral secondary amine and a solvent.

关键词： Asymmetric synthesis Solvent-controlled diastereodivergence Retro-aldol/aldol cascade reaction Spirooxindole N-Heterocyclic carbene catalysis

Organocatalytic asymmetric cascade cyclization reaction of o-hydroxy cinnamaldehydes with diphenylphosphine oxide

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Chinese Chemical Letters 2018年第11期29卷 1625-1628页

作者： Haiyun Sun Yuan Li Wei Liu Yang Zheng Zhengjie He The State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University Tianjin 300071 China Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) Tianjin 300071 China

A highly stereoselective asymmetric cascade cyclization reaction between o-hydroxycinnamaldehydes and diphenylphosphine oxide has been achieved with 84%-99% ee and 7：1-20：1 dr under the catalysis of L-diarylprolinol silyl ether. This reaction provides a facile access to highly enantioenriched 4- diphenylphosphinyl chroman-2-ols. It also represents a novel organocatalytic asymmetric phospha- Michael addition of α,β-unsaturated aldehydes with pentavalent P-nucleophiles.

关键词： Organocatalysis Asymmetric catalysis Cyclization reaction Phospha-Michael addition cascade reaction