Vinyl Esters Research Articles

Composite Recycling with Biocatalytic Thermoset Reforming.

Carbon fiber reinforced polymers (CFRPs, or composites) are increasingly replacing traditional manufacturing materials used in the automobile, aerospace, and energy sectors. With this shift, it is vital to develop end-of-life processes for CFRPs that retain the value of both the carbon fibers and the polymer matrix. Here we demonstrate a strategy to upcycle pre- and postconsumer polystyrene-containing CFRPs, cross-linked with unsaturated polyesters or vinyl esters, to benzoic acid. The thermoset matrix is upgraded via biocatalysis utilizing an engineered strain of the filamentous fungus Aspergillus nidulans, which gives access to valuable secondary metabolites in high yields, exemplified here by (2Z,4Z,6E)-octa-2,4,6-trienoic acid. Reactions are engineered to preserve the carbon fibers with much of their sizing so that the isolated carbon fiber plies are manufactured into new composite coupons that exhibit mechanical properties comparable to those of virgin manufacturing substrates. In sum, this represents the first system to reclaim a high value from both the fiber fabric and polymer matrix of a CFRP.

Rapid in situ carbon-13 hyperpolarization and imaging of acetate and pyruvate esters without external polarizer

Hyperpolarized 13C MRI visualizes real-time metabolic processes in vivo. In this study, we achieved high 13C polarization in situ in the bore of an MRI system for precursor molecules of most widely employed hyperpolarized agents: [1-13C]acetate and [1-13C]pyruvate ethyl esters in their perdeuterated forms, enhancing hyperpolarization lifetimes, hyperpolarized to P13C ≈ 28% at 80 mM concentration and P13C ≈ 19% at 10 mM concentration, respectively. Using vinyl esters as unsaturated Parahydrogen-Induced Polarization via Side-Arm Hydrogenation (PHIP-SAH) precursors and our novel polarization setup, we achieved these hyperpolarization levels by fast side-arm hydrogenation in acetone-d6 at elevated temperatures (up to 90°C) and hydrogenation pressures (up to 32 bar). We optimized the hyperpolarization process, reducing it to under 10 s, and employed advanced pulse sequences to enhance the polarization transfer efficiency. The hyperpolarization system has a small footprint, allowing it to be positioned in the same magnet, where 13C MRI is performed. We exemplified the utility of the design with sub-second in situ 13C MRI of ethyl [1-13C]pyruvate-d6. However, challenges remain in side-arm cleavage and purification in the MRI system to extract highly polarized aqueous agent solutions. Our results showcase efficient and rapid 13C hyperpolarization of these metabolite precursors in an MRI system with minimal additional hardware, promising to enhance future throughput and access to hyperpolarized 13C MRI.

Analysis of mechanical properties of basalt fabric reinforced fly ash filled vinyl ester composites using multi criteria decision making technique

The current research was to examine the mechanical properties of composite material made of vinyl ester filled with fly ash of various weight percentages. Before fabrication the amount of fly ash and resin were identified by using the Multi Criteria Decision Making technique (MCDM). The best filler weight percentage of 5 wt% is determined by using Weighted Aggregate Sum Product Assessment (WASPAS) which is one of the MCDM methods. The virgin samples of vinyl esters are mixed with weight of 5 wt%fly ash by incremental of 5 wt% up to 20 wt%. All the mechanical tests of the specimen were conducted as per ASTM standards. Subsequently based on the results from the WASPAS method of fly ash content, the basalt fabric was reinforced with fly ash filled vinyl ester to fabricate the hybrid composites. By the mixing of fly-ash with vinyl ester the strength of the fly ash filled composites has been found to be enhanced in the filler. The results from the mechanical testing signified that fly ash can be used as filler material in basalt fabric reinforced vinyl ester resin. The fly ash infused basalt fibre reinforced yields significant development in mechanical performance contrast to the other fabricated composites.

Block Copolymers of Poly(N-Vinyl Pyrrolidone) and Poly(Vinyl Esters) Bearing n-alkyl Side Groups via Reversible Addition-Fragmentation Chain-Transfer Polymerization: Synthesis, Characterization, and Thermal Properties.

Amphiphilic block copolymers of N-vinyl pyrrolidone (NVP) and various vinyl esters (VEs), PNVP-b-PVEs, namely vinyl butyrate (VBu), vinyl decanoate (VDc), and vinyl stearate (VSt), were synthesized through RAFT polymerization techniques. The sequential addition of the monomers methodology was employed starting from the polymerization of NVP followed by the polymerization of the Ves' monomer. The polymerization of NVP was conducted at 60 °C in benzene solution using AIBN as the initiator and O-ethyl S-(phthalimidylmethyl) xanthate as the CTA. The resulting PNVP macro-CTA was further applied for the polymerization of the vinyl ester in dioxane solution at 80 °C using, again, AIBN as the initiator. The block copolymers were characterized through size-exclusion chromatography (SEC) and NMR spectroscopy. The thermal behavior of the copolymers was studied by Differential Scanning Calorimetry (DSC), whereas their thermal stability via Thermogravimetric Analysis (TGA) and Differential Thermogravimetry (DTG).

An Exploratory Study of the Enzymatic Hydroxycinnamoylation of Sucrose and Its Derivatives.

Phenylpropanoid sucrose esters are a large and important group of natural substances with significant therapeutic potential. This work describes a pilot study of the enzymatic hydroxycinnamoylation of sucrose and its derivatives which was carried out with the aim of obtaining precursors of natural phenylpropanoid sucrose esters, e.g., vanicoside B. In addition to sucrose, some chemically prepared sucrose acetonides and substituted 3'-O-cinnamates were subjected to enzymatic transesterification with vinyl esters of coumaric, ferulic and 3,4,5-trimethoxycinnamic acid. Commercial enzyme preparations of Lipozyme TL IM lipase and Pentopan 500 BG exhibiting feruloyl esterase activity were tested as biocatalysts in these reactions. The substrate specificity of the used biocatalysts for the donor and acceptor as well as the regioselectivity of the reactions were evaluated and discussed. Surprisingly, Lipozyme TL IM catalyzed the cinnamoylation of sucrose derivatives more to the 1'-OH and 4'-OH positions than to the 6'-OH when the 3'-OH was free and the 6-OH was blocked by isopropylidene. In this case, Pentopan reacted comparably to 1'-OH and 6'-OH positions. If sucrose 3'-O-coumarate was used as an acceptor, in the case of feruloylation with Lipozyme in CH3CN, 6-O-ferulate was the main product (63%). Pentopan feruloylated sucrose 3'-O-coumarate comparably well at the 6-OH and 6'-OH positions (77%). When a proton-donor solvent was used, migration of the 3'-O-cinnamoyl group from fructose to the 2-OH position of glucose was observed. The enzyme hydroxycinnamoylations studied can shorten the targeted syntheses of various phenylpropanoid sucrose esters.

Application of Stemphylium lycopersici Extracts Immobilized on MCM-48type Mesoporous Materials as Biocatalysts for Monoacylglycerol Production.

Monoacylglycerols are eco-friendly and inexpensive emulsifiers with a range of applications. The traditional synthetic route is not eco-friendly, while enzymatic catalysis offers milder reaction conditions and higher selectivity. However, its application still is limited due to the costs. In this context, endophytic fungi can be source to new biocatalysts with enhanced catalytic activity. Based on this perspective, the aim of this study was perform the synthesis of MAG's through transesterification reactions of solketal and different vinyl esters, using crude and immobilized lipolytic extracts from the endophytic fungi Stemphylium lycopersici, isolated from Humiria balsamifera. The reactions were conducted using 100 mg of biocatalyst, 1 mmol of substrates, 9 : 1 n-heptane/acetone, at 40 °C, 200 rpm for 96 h. In the reactions using the ILE and stearate, laureate and decanoate vinyl esters it was possible to obtain the correspondent products with conversion rates of 52-75 %. Also, according to the structure drivers used in MCM-48 synthesis, different morphologies and conversions rates were observed. Employing [C16MI] Cl, [C14MI] Cl and [C4MI] Cl, the 1-lauroyl- glycerol conversion was 36 %, 79 % and 44 %, respectively. This is the first work involving the immobilization of an endophytic fungi and its utilization as a biocatalyst in the production of MAG's.

Cationic Alternating Copolymerization of Vinyl Esters and 3-Alkoxyphthalides: Side Chain-Crosslinkable Polymers for Acid-Degradable Single-Chain Nanoparticles.

Cationic copolymerization of vinyl acetate and 3-alkoxyphthalides (ROPTs) was demonstrated to proceed using GaCl3 as a Lewis acid catalyst. Both monomers did not undergo homopolymerization, while copolymerization smoothly occurred via the crossover reactions, resulting in alternating copolymers with molecular weights of over 104. The obtained copolymers could be degraded by acid due to the cleavage of the diacyloxymethine moieties, which were derived from the crossover reactions from vinyl acetate to ROPT, in the main chain. An advantage of not radical but cationic copolymerization of vinyl esters was exerted by copolymerizations of radically reactive group-containing vinyl esters with ROPTs. For example, vinyl cinnamate was successfully copolymerized with an ROPT by the cationic mechanism, while keeping the cinnamoyl groups intact. The obtained alternating copolymer was subjected to a photodimerization reaction of the cinnamoyl groups in the side chains, resulting in an acid-degradable single-chain nanoparticle via the intramolecular crosslinking reactions.

SYNTHESIS OF VINYL ESTERS OF SOME AROMATIC CARBOXYLIC ACIDS FROM VINYL ACETATE

In this work by the reaction of derivatives of benzoic acid containing substituents in the aromatic ring with vinyl acetate in the presence2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) vinyl esters of aromatic carboxylic acids have been synthesized. The influence of the nature of the initial compounds, temperature, zinc trifluoromethyl-sulfonate (Zn(OTf)2), dilithium 3,3′-diphenylbinaphtholate (3,3′-Ph2BINOL-2Li), tertiary potassium butylate (KOtrBu), butyllithium (BuLi) on the yield of synthesized compounds was investigated. The structure of the synthesized vinyl esters was proved by IR, 1H NMR, 13C NMR spectroscopies

Biocatalytic Regioselective O-acylation of Sesquiterpene Lactones from Chicory: A Pathway to Novel Ester Derivatives.

We report the first biocatalytic modification of sesquiterpene lactones (STLs) found in the chicory plants, specifically lactucin (Lc), 11β,13-dihydrolactucin (DHLc), lactucopicrin (Lp), and 11β,13-dihydrolactucopicrin (DHLp). The selective O-acylation of their primary alcohol group was carried out by the lipase B from Candida antarctica (CAL-B) using various aliphatic vinyl esters as acyl donors. Perillyl alcohol, a simpler monoterpenoid, served as a model to set up the desired O-acetylation reaction by comparing the use of acetic acid and vinyl acetate as acyl donors. Similar conditions were then applied to DHLc, where five novel ester chains were selectively introduced onto the primary alcohol group, with conversions going from >99 % (acetate and propionate) to 69 % (octanoate). The synthesis of the corresponding O-acetyl esters of Lc, Lp, and DHLp was also successfully achieved with near-quantitative conversion. Molecular docking simulations were then performed to elucidate the preferred enzyme-substrate binding modes in the acylation reactions with STLs, as well as to understand their interactions with crucial amino acid residues at the active site. Our methodology enables the selective O-acylation of the primary alcohol group in four different STLs, offering possibilities for synthesizing novel derivatives with significant potential applications in pharmaceuticals or as biocontrol agents.

Enzymatic synthesis of tyrosol esters in organic solvents and ionic liquids: Correlation between enzyme activity and solvent properties

Tyrosol is a principle phenolic compound present in olive oil and wine with great pharmacological potentials due to its strong antioxidant property. Its application can be highly extended by increasing its lipophilicity through esterification. In this study, tyrosol esters were synthesized by enzymatic transesterification of tyrosol with vinyl esters, with a commercial lipase from Novozymes (Novozym 435, Candida antarctica lipase B (CALB) immobilized on macroporous acrylic resin beads) as the catalyst, both in organic solvents and in ionic liquids. Methyl tert-butyl ether (MTBE) was the best solvent, offering complete conversions towards the synthesis of tyrosol esters with varying chain lengths (C2-C18) within 1 h. Taking the enzymatic transesterification between tyrosol and vinyl acetate as the model reaction, 18 organic solvents and 24 ionic liquids were screened, and their solvent properties (i.e. hydrophobicity, polarity, viscosity, water activity, and partition coefficients of substrate and product) were correlated to the enzyme activity. Upon enzyme screening, four new lipases were found to be highly efficient, relative to the best-performed Novozym 435 and Lipozyme TLIM (Thermomyces lanuginosus lipase (TLL) immobilized on silica gel), in tyrosol ester synthesis. This work provides enzymatic methods of esterifying tyrosol that are much more efficient than those reported in literature, and will shed light on re-consideration of the roles of solvents in nonaqueous enzymology.

Ligand and Substrate Effects on Regio‐ and Stereoselective Ru(II)‐Catalyzed Hydroacyloxylations to Vinylic Esters

AbstractTwo Ru(II)‐catalytic systems were developed for anti‐Markovnikov regioselective hydroacyloxylations of terminal alkynes to vinylic esters. [Ru(NCCH3)6][(BF4)2] favors (E)‐vinylic ester products with arylacetylenes and select carboxylic acids, whereas a Ru scorpionate complex with two electron‐withdrawing ligands favors (Z)‐vinylic ester isomers.

Synthesis of vinyl esters of some furan carboxylic acids based on vinyl acetate

Investigation of synthesized vinyl esters of several furancarboxylic acids: 2-furancarboxylic, 3-furancarboxylic, 5-formyl-2- furancarboxylic, 5-nitro-2-furanoic and 2,5-furandicarboxylic from vinyl acetate using the reaction vinyl substitution in the presence of the system: 2- chloro-4,6-dimethoxy-1,3,5-triazine, as well as Zn(OTf)2, 3,3’-Ph2BINOL- 2Li, KOtrBu and BuLi has been carried out. At the same time increasing of the catalytic activity of these systems was identified as following: 3,3’- Ph2BINOL-2Li < BuLi < KOtrBu < Zn(OTf)2. The influence of various factors on products yield was studied. Optimal conditions for the formation of vinyl esters of carboxylic acids were: temperature -30°C, the Zn(OTf)2 system, the molar ratio of carboxylic acid and vinyl acetate is 1:1.2. The yields of vinyl esters of the studied furancarboxylic acids has increased in the following order: vinyl ester of 5-nitro-2-furancarboxylic acid < vinyl ester of 5-formyl-2-furancarboxylic acid < vinyl ester of 2-furancarboxylic acid < vinyl ester of 3-furancarboxylic acid < vinyl ester 2 ,5- furandicarboxylic acid. The structure of the synthesized compounds was confirmed by IR, 1H, 13C spectroscopy and gas chromatography-mass spectrometry.

Biodegradable mPEG-b-poly(MDO-co-vinyl esters) block copolymers as a viable nanocarrier platform with tuneable disassembly

Xanthate-based copolymerisations of MDO and vinyl acetate-derivative monomers using a mPEG macroCTA created degradable amphiphilic block copolymers capable of self-assembly and crosslinking, where type of crosslinking influenced particle disassembly.

Reaction of aromatic carboxylic acids with phenylacetylene with the participation of a zinc catalyst

The reaction of benzoic, 4-methylbenzoic, 2-bromobenzoic and 4-bromobenzoic acids with phenylacetylene was carried out in a toluene solution at a temperature of 110 0C in the presence of a catalyst - 1 mol % [Zn(C4H7S2)4](NO3)2. In the coupling reaction of carboxylic acids with phenylacetylene a mixture of coupling products is formed according to the Markovnikov and anti-Markovnikov rules. A reaction mechanism was proposed and it was found that the yield of vinyl esters increased in the serie 4-CH3-C6H4COOH< C6H5COOH< 4-Br-C6H4COOH< 2-Br-C6H4COOH. It was found that with an increasing acidity of the carboxylic acids, the product formed by Markovnikov rule has been formed in a larger amount. On the contrary, as the acidity of the starting compounds decreased, the amount of the anti-Markovnikov coupling product has increased. The total yield of reaction products of phenylacetylene with carboxylic acid is 44% (65/35) in 4-methylbenzoic acid, 67% (80/20) in benzoic acid, 78% (82/18) in 4-bromobenzoic acid, 82% (85 /15) in 2-bromobenzoic acid. The structure of the synthesized vinyl esters was proved on the base of the analysis of IR, 1H, 13C NMR and Mass spectrums.

Development of nanoparticles based on amphiphilic cyclodextrins for the delivery of active substances

Although amphiphilic cyclodextrin derivatives (ACDs) serve as valuable building blocks for nanomedicine formulations, their widespread production still encounters various challenges, limiting large-scale manufacturing. This work focuses on a robust alternative pathway using mineral base catalysis to transesterify β-cyclodextrin with long-chain vinyl esters, yielding ACD with modular and controlled hydrocarbon chain grafting. ACDs with a wide range of degrees of substitution (DS) were reliably synthesized, as indicated by extensive physicochemical characterization, including MALDI-TOF mass spectrometry. The influence of various factors, including the type of catalyst and the length of the hydrocarbon moiety of the vinyl ester, was studied in detail. ACDs were assessed for their ability to form colloidal suspensions by nanoprecipitation, with or without PEGylated phospholipid. Small-angle X-ray scattering and cryo-electron microscopy revealed the formation of nanoparticles with distinct ultrastructures depending on the DS: an onion-like structure for low and very high DS, and reversed hexagonal organization for DS between 4.5 and 6.1. We confirmed the furtivity of the PEGylated versions of the nanoparticles through complement activation experiments and that they were well tolerated in-vivo on a zebrafish larvae model after intravenous injection. Furthermore, a biodistribution experiment showed that the nanoparticles left the bloodstream within 10 h after injection and were phagocytosed by macrophages.

Prospects in the application of a frontally curable epoxy resin for cured‐in‐place‐pipe rehabilitation

AbstractPhotocurable acrylates and vinyl esters are among the most commonly used resins in cured‐in‐place‐pipe (CIPP) rehabilitation technology, as they impart excellent thermomechanical properties in composite pipes. In the quest for achieving a higher energy efficiency of the photo‐curing process in CIPP, the frontal polymerization technique is a viable alternative that requires a lower irradiation dosage coupled with exceptionally high curing speeds and depths. Herein, for the first time, we report the application of frontal polymerization in the rehabilitation of underground pipes using a newly developed frontally curable epoxy‐based resin (Trelleborg Self‐Curing*). The neat resin is characterized for degree of cure, glass transition temperature, and mechanical properties via FTIR, DMA, and tensile tests, respectively. In a comprehensive way, the properties are benchmarked against commercially available acrylate (Trelleborg Light Cure*) and vinyl ester (Trelleborg Rapid Cure*) resins to evaluate their applicability for CIPP. The results show a higher glass transition temperature and final monomer conversion for the frontally cured resin, which cures significantly faster than the reference resins under the same irradiation conditions. In proof‐of‐concept trials, the newly developed resin successfully cures polymeric liners in a PVC host pipe with 100% water tightness and without losing its structural integrity. Results from ring stiffness tests for cured composite pipes additionally show that liners cured with Trelleborg Self‐Curing* resin pass the minimum required Young's modulus for non‐pressure drainage pipes as per ASTM F1216. Thus, frontally curable epoxy‐based resins are a promising and competitive alternative to acrylates and vinyl esters in CIPP.

Exceptionally Mild and High-Yielding Synthesis of Vinyl Esters of Alpha-Ketocarboxylic Acids, Including Vinyl Pyruvate, for Parahydrogen-Enhanced Metabolic Spectroscopy and Imaging.

Metabolic changes often occur long before pathologies manifest and treatment becomes challenging. As key elements of energy metabolism, α-ketocarboxylic acids (α-KCA) are particularly interesting, e.g., as the upregulation of pyruvate to lactate conversion is a hallmark of cancer (Warburg effect). Magnetic resonance imaging with hyperpolarized metabolites has enabled imaging of this effect non-invasively and in vivo, allowing the early detection of cancerous tissue and its treatment. Hyperpolarization by means of dynamic nuclear polarization, however, is complex, slow, and expensive, while available precursors often limit parahydrogen-based alternatives. Here, we report the synthesis for novel 13C, deuterated ketocarboxylic acids, and a much-improved synthesis of 1-13C-vinyl pruvate-d6, arguably the most promising tracer for hyperpolarizing pyruvate using parahydrogen-induced hyperpolarization by side arm hydrogenation. The new synthesis is scalable and provides a high yield of 52%. We elucidated the mechanism of our Pd-catalyzed trans-vinylation reaction. Hydrogenation with parahydrogen allowed us to monitor the addition, which was found to depend on the electron demand of the vinyl ester. Electron-poor α-keto vinyl esters react slower than "normal" alkyl vinyl esters. This synthesis of 13C, deuterated α-ketocarboxylic acids opens up an entirely new class of biomolecules for fast and cost-efficient hyperpolarization with parahydrogen and their use for metabolic imaging.

Preparation of Thermoplastic Cellulose Esters in [mTBNH][OAC] Ionic Liquid by Transesterification Reaction.

The transesterification of cellulose with vinyl esters in ionic liquid media is suggested as a prospective environmentally friendly alternative to conventional esterification. In this study, various long-chain cellulose esters (laurate, myristate, palmitate, and stearate) with a degree of substitution (DS) up to 1.8 have been synthesized in novel distillable ionic liquid, [mTBNH][OAC]. This IL has high dissolving power towards cellulose, which can improve homogeneous transesterification. Additionally, [mTBNH][OAC] has durability towards recycling and can be regenerated and re-used again for the next cycles of esterification. DMSO is used as a co-solvent because of its ability to speed up mass transport due to lower solvent viscosity. The optimization of the reaction parameters, such as co-solvent content, temperature (20-80 °C), reaction time (1-5 h), and a molar ratio of reactants (1-5 eq. AGU) is reported. It was found that within studied reaction conditions, DS increases with increasing reaction time, temperature, and added vinyl esters. Structure analysis using FTIR, 1H, and 13C NMR after acylation revealed the introduction of the alkyl chains into cellulose for all studied samples. The results also suggested that the substitution order of the OH group is C7-O6 > C7-O2 > C7-O3. Unique, complex thermal and rheological investigation of the cellulose esters shows the growth of an amorphous phase upon the degree of substitution. At the same time, the homogeneous substitution of cellulose with acyl chains increases the melt viscosity of a material. Internal plasticization in cellulose esters was found to be the mechanism for the melt processing of the material. Long-chain cellulose esters show the potential to replace commonly used externally plasticized cellulose derivatives.

Condition optimization and kinetic evaluation of Novozym 435-catalyzed synthesis of aroma pyridine esters

A new method for rapid synthesis of pyridine esters without stirring based on Novozym 435 catalysis had been reported, which was from pyridine methanols and vinyl esters. Based on single factor experiment, the optimization of the enzymatic transesterification was received by response surface methodology (RSM). The high yield of 82% was still reached when Novozym 435 had been recycled 12 times. Under optimal conditions, a total of 22 pyridine esters were synthesized. The kinetic model of Novozym 435-catalyzed transesterification of vinyl acetate with 3-pyridinemethanol was established by enzymatic assay. It was discovered that the reaction followed the Ping-Pong Bi-Bi mechanism, and 3-pyridinemethanol inhibited the reaction. Gas chromatography-mass spectrometry-olfactometry (GC–MS-O) was used to analyze the synthesized pyridine esters, of which pyridin-3-ylmethylhexanoate (3e), pyridin-3-ylmethylcinnamate (3i), and 2-(pyridin-2-yl)ethyl acetate (3 s) possessed strong and excellent aromas. These three flavor compounds (3e, 3i and 3 s) were found to have good stability at the specified temperature by thermogravimetric (TG) analysis.

Discovery of acylated isoquercitrin derivatives as potent anti-neuroinflammatory agents in vitro and in vivo

Neuroinflammation is considered as an important pathological mechanism in neurodegenerative diseases. The natural isoquercitrin (IQ) was reported to have potential anti-neuroinflammatory activity. The acylation of glycoside in IQ enhanced its hydrophobicity, which was expected to enhance the protective effect against inflammation. In this study, three carboxylic acids with anti-neuroinflammatory effects including cinnamic acid, ibuprofen (IBU) and acetylsalicylic acid were introduced into the 6''-OH of IQ through the corresponding vinyl esters intermediates (8a-8c). Ultimately, the acylated IQ derivatives (Compound 9a-9c) were obtained with 35–42% yields using immobilized lipase Novozym 435 as catalyst. Subsequently, their anti-neuroinflammatory activities were evaluated in lipopolysaccharide (LPS)-induced BV2 cells. Compound 9b improved cell viability in the range of ≤50 μM and significantly decreased NO, PGE2 production and TNF-α, IL-1β release and oxidative stress level with a concentration-dependent manner. Also, it could downregulate iNOS, COX-2, TNF-α and IL-1β expression levels, approximately 40% reduction were achieved when 15μM compound 9b was employed. In addition, compound 9b resisted phosphorylation and degradation of IkBαs, suppressing the activation of NF-κB signaling pathway, exhibiting excellent neuroinflammatory inhibition. Moreover, the administration of compound 9b (30, 60 mg/kg) alleviated behavioral disorders and neuronal damages in LPS-induced neuroinflammatory mice. Meanwhile, the decreased TNF-α, IL-1β release, expression and the inhibited glial cells activation were obtained in compound 9b-treated group, which was superior to that of IQ or IBU. Overall, these findings demonstrated that compound 9b, formed by the introduction of ibuprofen into IQ, can serve as a novel promising therapeutic agent for anti-neuroinflammation.