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SYNLETT · 2018 ·Vol. 29 ·期 09 ·1244-1248 · IF 2.369

PPh3-Mediated [3+2] Cycloaddition Reaction between Bis-Substituted Allenoate and N-Tosylaldimines to Construct 2-Pyrrolines

Xiangwen Kong,Lihua Liu,Siqin Luo,Shilu Fan,Haisheng Qian,Hua Xiao

A triphenylphosphine-promoted [3+2] cycloaddition of α,γ-bis-substituted allenoates and N-tosylaldimines followed by alkene isomerization was disclosed, affording a series of functionalized 2-pyrroline derivatives in moderate chemical yields with random diastereoselectivities.

研究领域: 有机化学 · 药物化学 · 合成方法学 · 杂环化学
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NEW JOURNAL OF CHEMISTRY · 2023 ·Vol. 47 ·期 26 ·12296-12303 · IF 3.3

Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions

Wen-Hui Zhang,Zi-Yue Chen,Ren-Ming Liu,Xiong-Wei Liu,Bo-Wen Pan,Jian Zhou,Ying Zhou,You-Ping Tian,Xiong-Li Liu

Herein, previously unreported trimethylindolenines serving as useful C–N synthons in [3+2] cycloaddition reactions of donor–acceptor 3-isothiocyanato oxindoles to build a library of spiro[oxindole-thioxoimidazolidine-indoline] hybrids are described. A wide range of intriguing and complex products bearing three pharmacophores and three adjacent quaternary stereocentres were smoothly afforded in up to 92% yield, >20 : 1 dr, under catalyst-free conditions. Moreover, this strategy further expands the skeletal diversity of polyheterocycles, which will aid the search for new bioactive molecules.

CAS / MDL: 14913-33-8
研究领域: 有机化学 · 药物化学 · 合成化学
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MATERIALS & DESIGN · 2022 · IF 9.417

Using a photodriven radical-mediated [3 + 2] cyclization reaction to prepare embolic microspheres from sucrose allyl ether without degradative chain transfer

Yanfang Zhou,Mianrong Chen,Piaoyi Chen,Xiaotian Zhao,Hua Zhou,Jingmiao Wu,Xufeng Li,Qiuxia Li,Runxing Lin,Yugang Huang,Yingying Lun,Guodong Ye

Preparing polymers from allyl monomers without being hindered by degradative chain transfer (DCT) remains a challenge. Herein, we report the synthesis and characterization of embolic microspheres based on allyl monomers for transcatheter arterial embolization using a photodriven radical-mediated [3 + 2] cyclization reaction (PRMC) without metal catalysis. The mechanism of PRMC was validated by thermal and spectral experiments, indicating that PRMC overcomes the restrictions of DCT and makes it possible to synthesize a variety of well-defined polymers from inert allyl monomers. The embolization microspheres based on poly(sucrose allyl ether) were characterized by morphological determination, degradation and swelling tests. Cell experiments show that the microspheres have good biocompatibility. The complete arterial occlusion of the embolized kidneys was observed, indicating that microspheres have broad application prospects in embolization interventional therapy.

研究领域: 高分子化学 · 介入医学 · 材料科学
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SYNTHETIC COMMUNICATIONS · 2019 · IF 1.439

One-pot multicomponent construction of chromanone-fused pyrrolidinyl spirooxindole collections through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction

Shuang Chen,Jing Yue,Xiong-Li Liu,Jun-Xin Wang,Xiong Zuo,Yu Cao

A new method was developed for the facile one-pot multicomponent construction of heterocycle-fused spiro compounds containing chromanone and pyrrolidinyl spirooxindoles, two potential pharmacophores, in one molecule through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction of carboxylic acid group-activated chromones 1 with isatin-derivated azomethine ylides based on molecular hybridization strategy. A wide variety of products with three contiguous stereocenters including a spiro quaternary stereocenter were smoothly prepared with high efficiency (up to 87% yield and 20:1 diastereomeric ratio). This method could offer libraries of architecturally diverse and multiple pharmacore collections, potentially useful in medicinal chemistry.

CAS / MDL: 14913-33-8
研究领域: 有机化学 · 药物化学 · 合成化学
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APPLIED SURFACE SCIENCE · 2009 · IF 1.576

A versatile method for the preparation of end-functional polymers onto SiO2 nanoparticles by a combination of surface-initiated ATRP and Huisgen [3 + 2] cycloaddition

J.C. Chen,W.Q. Luo,H.D. Wang,J.M. Xiang,H.F. Jin,F. Chen,Z.W. Cai

A versatile method was developed for the chain-end functionalization of the grafted polymer chains for surface modification of nanoparticles with functionalized groups through a combination of surface-initiated atom-transfer radical polymerization (ATRP) and Huisgen [3   +   2] cycloaddition. First, the surface of SiO 2 nanoparticles was modified with poly(methyl methacrylate) (PMMA) brushes via the “grafting from” approach. The terminal bromides of PMMA-grafted SiO 2 nanoparticles were then transformed into an azide function by nucleophilic substitution. These azido-terminated PMMA brushes on the nanoparticle surface were reacted with alkyne-terminated functional end group via Huisgen [3   +   2] cycloaddition. FTIR and 1 H NMR spectra indicated quantitative transformation of the chain ends of PMMA brushes onto SiO 2 nanoparticles into the desired functional group. And, the dispersibility of the end-functional polymer-grafted SiO 2 nanoparticles was investigated with a transmission electron microscope (TEM).

研究领域: 材料科学 · 高分子化学
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NEUROREPORT · 2018 ·Vol. 29 ·期 5 ·432 · IF 1.266

Disruption of the GluA2/GAPDH complex using TAT-GluA2NT1-3-2 peptide protects against AMPAR-mediated excitotoxicity after epilepsy

Zhang Jinghui,Qiao Nana,Ding Xiufang,Wang Jiwen

Excitotoxicity and neuronal death following epilepsy involve α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors (AMPARs). It forms a protein complex with glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and co-internalizes upon activation of AMPA receptors after epilepsy. Disruption of the GluA2 /GAPDH complex with an interfering peptide , TAT- GluA2 NT1-3-2 , protects cells against AMPAR-mediated excitotoxicity, which have been identified in in-vitro and in-vivo models of brain ischemia. We postulated that disruption of the GluA2 /GAPDH interaction with the TAT- GluA2 NT1-3-2 peptide would also protect against AMPAR-induced neuronal injury in an in-vivo model of status epilepticus (SE). In the present study, we divided pilocarpine -induced SE Wistar rats into three main groups: the TAT- GluA2 NT1-3-2 peptide group, the TAT- GluA2 NT-scram peptide group, and the normal saline group, and injected different doses of peptides stereotaxically into the hippocampus of SE rats to investigate whether the GluA2 /GAPDH interaction could be disrupted by our TAT- GluA2 NT1-3-2 peptide and determine its most appropriate dose. Then, the dose was administered stereotaxically at different time points after SE to determine the best administration time of neuronal protection. We found that the TAT- GluA2 NT1-3-2 peptide can disrupt the GluA2 /GAPDH interaction and protects against epilepsy-induced neuronal damage. The GluA2 /GAPDH interaction may be a novel therapeutic target for epilepsy.

CAS / MDL: 54-71-7
研究领域: 神经科学 · 药理学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Probiotics and Antimicrobial Proteins · 2024 · IF 4.4

Study on the Mechanism of Bifidobacterium animalis subsp. lactis F1-3–2 Regulating Bile Acid Metabolism Through TMA-TMAO Pathway to Improve Atherosclerosis

Zheng Xiumei,Zhang Zhe,Shan Tianhu,Zhao Maozhen,Lu Haiyan,Zhang Lanwei,Liang Xi

Atherosclerosis is a major cause of cardiovascular disease (CVD). The trimethylamine (TMA)-trimethylamine N-oxide (TMAO) pathway is a key crossover pathway highly associated with diet, gut microbiome, and atherosclerosis. The Bifidobacterium animalis subsp. lactis F1-3–2 ( Bif. animalis F1-3–2, No. CCTCCM2020832) was screened through in vitro and in vivo experiments in the early stage of this study with excellent lipid-lowering and anti-inflammatory function. By building an atherosclerosis model and focusing on TMAO, the specific mechanism of Bif. animalis F1-3–2 to improve atherosclerosis was explored. The study found that Bif. animalis F1-3–2 effectively improved the accumulation of aortic plaque in atherosclerotic mice. The strain improved lipid metabolism in serum and liver. It decreased the serum TMA and TMAO, regulated bile acid composition, participated in the farnesoid X receptor (FXR) pathway to improve lipid metabolism, and further reduced the aortic macrophage foam cell accumulation. In addition, the strain could improve the structure of the intestinal microbiome and reduce the proportion of Firmicutes and Bacteroidetes. The abundance of Turicibacter , Clostridium sensu stricto_1 , and Romboutsia was reduced at the genus level. The differential microbiota is highly correlated with bile acid metabolism, which is speculated to be involved in ameliorating atherosclerotic lipid metabolism disorders. Graphical abstract

研究领域: 微生物学 · 心血管疾病 · 营养学 · 代谢组学
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International Journal of Electrochemical Science · 2023 · IF 1.5

A Novel Solid-State Electrochemiluminescence Sensor Based on poly(3-amino-4 hydroxybenzenesulfonic acid) /Ru(bpy)3 2+ Modified Electrode for Determination of Malachite Green

Qiu-feng Lan,Wen-chang Wang,Xiao-hui Chen,Zhi-dong Chen

The poly(3-amino-4-hydroxybenzenesulfonic acid)/Ru(bpy) 3 2+ modified glassy carbon electrode (PAHBS/Ru(bpy) 3 2+ /GCE) is a novel solid-state electrochemiluminescence (ECL) sensor. It was prepared by electropolymerization of 3-amino-4-hydroxybenzenesulfonicacid (AHBS) followed by soaking into Ru(bpy) 3 2+ solution. Ru(bpy) 3 2+ was entrapped on the electrode via the electrostatic interactions between sulfonic acid groups and Ru(bpy) 3 2+ cation. The morphology and composition of the modified electrodes were analysed using scanning electron microscope and energy-dispersed spectrum. Cyclic voltammetry and electrochemical impedance spectroscopy were used to compare the electrochemical behavior of the electrodes before and after modification. Under the optimal conditions, the ECL intensity of the quenching value (ΔECL) versus the logarithm of the concentration of malachite green (MG) was linear over a concentration range from 5.0 × 10 -8 to 1.0 × 10 -5 mol L -1 ( r = 0.9931) and the limit of detection (LOD) was 2.5 × 10 -8 mol L -1 . This method has been successfully applied to the determination of MG in pond water.

研究领域: 分析化学 · 环境科学
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MICROCHIMICA ACTA · 2017 ·Vol. 184 ·期 7 ·2325-2331 · IF 4.58

Synthesis of silica nanoparticles doped with [Ru(bpy)3]2+ and decorated with silver nanoclusters for the ratiometric photoluminescent determination and intracellular imaging of Cu(II) ions

Huang Xinan,Jiang Hong,Li Yongxin,Sang Lijia,Zhou Huipeng,Shahzad Sohail Anjum,Ibupoto Zafar Hussain,Yu Cong

A sensitive and selective luminescent nanoprobe (referred to as DEPN) is designed for the determination of Cu(II) ions. DEPN shows two emission peaks, one at 602 nm and caused by [Ru(bpy) 3 ] 2+ , the other (peaking at 500 nm) caused by silver nanoclusters (AgNCs). The luminescence of the ruthenium complex is inert and acts as the internal reference signal, while that of the AgNCs is quenched by Cu(II) ions. Under 350 nm photoexcitation, a linear relationship is found between the ratio of emission intensity (I 500 /I 602 ) and the concentration of Cu(II) ions in the 0.1–16 μM range. The detection limit of Cu(II) ions is estimated to be 50 nM. The DEPN was applied to the determination of Cu(II) ions in (spiked) water samples, and to intracellular imaging of Cu(II) in HeLa cells using confocal fluorescence microscopy. Schematic presentation of a dual-emission photoluminescence nanoprobe for selective Cu 2+ sensing. The emission of the Ag nanoclusters (at 500 nm) is quenched by Cu 2+ , while that of the Ru(bpy) 3 2+ -doped silica nanoparticles (at 602 nm) remains unchanged and serves as a reference.

CAS / MDL: 9002-98-6 78-10-4
研究领域: 纳米技术 · 分析化学 · 材料科学 · 生物医学工程 · 细胞生物学
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ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES · 2022 ·Vol. 238 ·期 1 ·13-14 · IF 0.365

The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O

Zhihong Zhu,Lilei Zhang

C 14 H 12 BrClN 2 O, monoclinic, P 2 1 / c (no. 14), a  = 13.4072(6) Å, b  = 8.6103(5) Å, c  = 12.3824(6) Å, β  = 100.475(4), V  = 1405.60(12) Å 3 , Z  = 4, R gt ( F ) = 0.0499, wR ref ( F 2 ) = 0.1215, T = 173 K.

研究领域: 化学 · 晶体学
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SYNTHESIS-STUTTGART · 2020 ·Vol. 53 ·期 07 ·1341-1348 · IF 2.675

Photoinduced [3+2] Annulation of Alkene with o-Iodoanilines: An Expedient Approach to Indolines

Xinxin Zhao,Lin Guo,Chao Yang,Wujiong Xia

A highly regioselective [3+2] cyclization of alkenes with 2-iodoanilines under the irradiation of UV light is described. This general, metal-free strategy facilitates the direct preparation of 2-mono-/disubstituted indolines as well as spiroindolines through alkene carboamination in one step. Mechanistic studies suggested that the photochemical protocol proceeded via a radical pathway.

研究领域: 有机化学 · 合成化学
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PEST MANAGEMENT SCIENCE · 2020 ·Vol. 76 ·期 9 ·2978-2985 · IF 3.75

Antifungal effects of 3-(2-pyridyl)methyl-2-(4-chlorphenyl) iminothiazolidine against Sclerotinia sclerotiorum

Xianfei Zhang,Jiuyong Xu,Solange Muhayimana,Hui Xiong,Xuefeng Liu,Qingchun Huang

BACKGROUND Sclerotinia stem rot (SSR) caused by Sclerotinia sclerotiorum threatens oilseed rape cultivation, and the emergence of fungicide-resistant strains has led to control failures worldwide. Identifying novel chemical alternatives with different modes of action and high antifungal activities is thus crucial. Herein we evaluated the antifungal effects of 3-(2-pyridyl)methyl-2-(4-chlorphenyl)imino- thiazolidine (PMAS) on S. sclerotiorum to determine its efficacy for SSR management. RESULTS PMAS had an inhibitory effect on mycelial growth; the EC 50 values were 17.83 and 21.15 μg mL −1 for the carbendazim-susceptible strain Ss01 and carbendazim-resistant strain Hm25, respectively. PMAS treatment changed the color of inhibited mycelia to green, and the hyphae were sustained in the undifferentiated stage. Cysteine supplementation made this green color disappear, whereas methionine enhanced the color. Moreover, PMAS treatment markedly inhibited oxalic acid biogenesis, increased free thiol content in mycelia, and weakened the activities of oxaloacetase and malate dehydrogenase, but had little effect on the activity of glyoxylate dehydrogenase. Cysteine could reverse the inhibitory effects of PMAS on mycelial morphogenesis and biochemical constituents, except thiol production. In the pot-culture experiment, PMAS showed a good protective effect, with the control efficacy being >91% on SSR. CONCLUSION PMAS appears to be an effective fungicide for SSR management. © 2020 Society of Chemical Industry

研究领域: 植物病理学 · 农学 · 分子生物学
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