Acrylic Acid Derivatives Research Articles

Lateral Organization of Lipid Membranes Induced by Amphiphilic Polymer Inclusions

Polymers belonging to a set of amphiphilic poly(acrylic acid) derivatives of varying hydrophobicity and charge density have recently been shown to slowly break small lipid vesicles and stabilize for hours or days transient mixed states such as membrane sheets, aggregates of mixed micelles, integral membrane proteins complexes, and so forth. We used giant unilamellar vesicles labeled with fluorescent probes to observe the evolution of a whole lipid-membrane including nondisruptive events, during the polymer-induced transition. The effect on the lipid bilayer depended strongly on the chemical structure and the concentration of polymer. Polymers of high hydrophobicity needed hours to disrupt the membranes. Before breakage, we observed intermediate states such as buds and filaments. Using less hydrophobic polymers, formation of flat domains was observed over hours at high polymer concentration (0.5 g/L). A single vesicle combined, over a few tens of micrometers, both curved fluorescent zones and flat zones of...

Optimisation of carbomer viscous eye drops: an in vitro experimental design approach using rheological techniques

The optimisation of the in vitro interaction between several poly(acrylic acid) derivatives (Carbopol ® 1342P NF, Carbopol ® 974P and Carbopol ® 980 NF) and mucin was performed by an analysis technique combining oscillatory shear rheology and experimental design in order to improve the formulation of carbomer viscous eye drops. First, standard oscillation procedures were used to characterise the polyacrylic acid and mucin dispersions, and to investigate the influence of several polymer-related factors (concentration, preparation, type of polymer used) on the rheological properties. Second, an experimental plan design was developed to investigate the effect of polymer-related factors on the mucoadhesive indexes (MAI ( G′) and MAI ( G″) ) which were calculated using the viscoelastic data obtained from polymer/mucin, polymer/tearfluid and mucin/tearfluid mixtures. Optimal mucoadhesive interactions were determined based on the experimental design results. Finally, the optima were fully characterised rheologically to further verify the mucoadhesive capacity. The main conclusion is that the factor influencing most explicitly the mucoadhesive interaction of the viscous eye drop is the mucin concentration and neither the type of polyacrylic acid, nor its concentration.

Isatin derivatives are reactive electrophilic components for the Baylis–Hillman reaction

Isatin derivatives readily react as the electrophilic component in the Baylis–Hillman reaction giving good to excellent yields of the respective adducts. It is generally accepted that ketones only take part in the Baylis–Hillman reaction under relatively extreme conditions, with a few exceptions. Isatin on the other hand readily reacts with acrylic acid derivatives in ethanol and or ethanol/THF mixtures in the presence of a catalytic quantity of DABCO. The solid state structures for these novel dioxindole derivatives were determined for two adducts by single-crystal X-ray diffraction spectroscopy, revealing an inside hydroxyl conformation.

3+2]-Cycloaddition of 2-(tert-butylsulfanyl)propenoic acid derivatives to cyclooctyne

The title compounds 1a,b being α-acceptor-substituted tert-butyl vinylsulfides add to cyclooctyne; upon warming dioxane solutions of 1a,b for two days 2,3,4,5,6,7,8,9- octahydrocycloocta(b)thiophenes 7a,b were formed in good yield, accompanied by loss of isobutene.

ChemInform Abstract: Application of Polymers and Copolymers of the Derivatives of Acrylic Acid and Ethylene Oxide in Pharmaceutics

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ChemInform Abstract: Transition Metal Catalyzed Addition of Amines to Acrylic Acid Derivatives. A High‐Throughput Method for Evaluating Hydroamination of Primary and Secondary Alkylamines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

New Phosphorus−Carbon Cage Compounds by Diels−Alder and Homo Diels−Alder Reactions of 1,3,5-Triphosphabenzenes with Alkenes

Ethylene, various monosubstituted alkenes (acrylic acid derivatives, styrene), as well as some selected disubstituted alkenes (maleic acid derivatives, fumaric acid derivatives, norbornene, cyclopentadiene) undergo Diels−Alder reactions with the 1,3,5-triphosphabenzenes 1 under mild conditions to furnish the dihydrotriphosphabarrelenes 9, 11a−c, 13a−e, 15a−d, 17a,b, and 24. The monoadduct 26 as well as the diadducts 27 and 28 are isolated following the reaction with norbornadiene. Cyclopropene is the only alkene to undergo a Diels−Alder/homo Diels−Alder reaction sequence to afford the hexacyclic system 20.

Transition Metal-Catalyzed Addition of Amines to Acrylic Acid Derivatives. A High-Throughput Method for Evaluating Hydroamination of Primary and Secondary Alkylamines

Several new classes of transition metal-catalyzed reactions of amines with the CC bond of acrylic acid derivatives were discovered using a high-throughput colorimetric assay. This assay is general for the reactions of primary and secondary alkylamines with acrylic acid derivatives, and the screening of potential catalysts using this assay revealed a number of different metal/ligand combinations that promote these hydroaminations. The colorimetric assay revealed catalysts for the addition of piperidine to methacrylonitrile, crotononitrile, ethyl crotonate, and ethyl methacrylate, as well as catalysts for reactions of butylamine and aniline with methacrylonitrile. A catalyst for the addition of aniline to crotononitrile at 100 °C was also discovered. The products of these reactions are basic building blocks for the synthesis of β-amino acids, amino alcohols, and diamines. These reactions may ultimately produce an enantioselective route to optically active difunctional materials from commodity reagents.

Antimicrobial and Hemostatic Effects of Silver-Containing Poly(acrylic acid) Derivatives

Antimicrobial and Hemostatic Effects of Silver-Containing Poly(acrylic acid) Derivatives

Ab initio and Density Functional Calculations on the Ring-Chain Tautomerism of γ-Oxocarboxylic Acids

The results of ab initio (HF, MP2) and density functional (B3LYP) calculations on a series of γ-oxocarboxylic acids [(Z)-3-acetyl or benzoylacrylic and 2-acetyl or benzoylbenzoic acids] A and their cyclic tautomers B are presented. For the open-chain tautomers, different rotamers were considered. Bulk solvent effects were considered by using the polarised continuum model (PCM) and were found to be essential for a proper description of the ring-chain tautomeric equilibrium. Acetyl derivatives generally prefer the cyclic form, whereas for benzoyl derivatives the preference depends on the nature of the link. Introduction of substituents (methyl, phenyl) at C2 and/or C3 for acrylic acid derivatives substantially shifts the equilibrium towards the cyclic form B.

A New Diphosphane Derived from Carbohydrates as an Effective Ligand for Asymmetric Hydrogenation

A novel chiral diphosphane derived from D-(+)-xylose, 3,5-dideoxy-1,2-O-isopropylidene-3,5-bis(diphenylphosphanyl)-α-D-xylofuranose (Xylophos), and its cationic cyclooctadiene rhodium(I) complex have been synthesised and characterised. Excellent results were obtained with Xylophos in the asymmetric Rh-catalysed hydrogenation of acrylic acid derivatives (ee′s up to 98%). Hydrogenation results are explained in terms of the structure of the precatalyst [Rh(cod)(Xylophos)]+BF4−.

Solid-phase synthesis of 1,2,3,4-tetrahydro-2-pyridones via aza-annulation of enamines.

An efficient solid-phase approach has been developed to prepare nitrogen heterocycles with a 1,2,3,4-tetrahydro-2-pyridone core via aza-annulation of enamines. Immobilized enamines were prepared from the reaction of primary amines with propynoic acid derivatives or ketones. Aza-annulation reactions were carried out by reacting resin-bound enamines with symmetrical alpha,beta-unsaturated acid anhydrides or alpha,beta-unsaturated acids in the presence of DPPA and TEA. The annulation products were isolated in good to high crude yields. Influence of sterically hindered amines as well as alpha- and beta-substituted acrylic acid derivatives on the annulation reaction was also investigated.

Ruthenium Carbene Complexes with N,N‘-Bis(mesityl)imidazol-2-ylidene Ligands: RCM Catalysts of Extended Scope

The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes. They also apply to annulations that are beyond the scope of the standard Grubbs carbene 1 as well as to ring-closing reactions of acrylic acid derivatives even if the resulting alpha,beta-unsaturated lactones (or lactams) are tri- or tetrasubstituted. The reactivity of 3a was found to be highly dependent on the reaction medium: particularly high reaction rates are observed in toluene, although this solvent also leads to an increased tendency of the catalyst to isomerize the double bonds of the substrates.

Diphosphite ligands based on ribose backbone as suitable ligands in the hydrogenation and hydroformylation of prochiral olefins

Rh(I) and Ir(I) cationic complexes [M(cod)(PP)]BF 4 have been synthesised from diphosphite ligands 4– 6 derived from ribofuranose. They have been used in the rhodium and iridium catalysed asymmetric hydrogenation of acrylic acid derivatives. Ribose derivative ligands 4– 6 have also been used as auxiliaries in the Rh-catalysed hydroformylation of styrene. Hydroformylation results have been explained on the basis of the species formed under hydroformylation conditions. Comparative experiments with the related epimer d-(+)-xylose derivatives showed that the configuration of the product is controlled by the absolute configuration of the stereogenic carbon atom C-3.

Oligomerization of Acrylic Acid Derivatives by a Reaction with the Alkylcopper(I)-Phosphine Complex

Reaction of alkylcopper(I)phosphine complexes with electron-deficient olefins affected preferentially the products based on oligomerization, e.g. the product obtained by sequential conjugated addition, trimerization and cyclization from methyl methacrylate and the dimerization product from butyl acrylate.

Synthesis of polyacrylamides N-substituted with PNA-like oligonucleotide mimics for molecular diagnostic applications.

Two types of oligonucleotide mimics relative to peptide nucleic acids (PNAs) were tested as probes in nucleic acid hybridisation assays based on polyacrylamide technology. One type of mimic oligomers represented a chimera constructed of PNA and phosphono-PNA (pPNA) monomers, and the other one contained pPNA residues alternating with PNA-like monomers on the base of trans -4-hydroxy-L-proline (HypNA). A chemistry providing efficient and specific covalent attachment of these DNA mimics to acrylamide polymers using a convenient approach based on the co-polymerisation of acrylamide and some reactive acrylic acid derivatives with oligomers bearing 5'- or 3'-terminal acrylamide groups has been developed. A comparative study of polyacrylamide conjugates with oligonucleotides and mimic oligomers demonstrated the suitability and high potential of PNA-pPNA and HypNA-pPNA chimeras as sequence-specific probes in capture and detection of target nucleic acid fragments to serve current forms of DNA arrays.

Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine

Reactivities of 10-propynyl-9(10H)-acridone toward various aldehydes in BF3·Et2O-promoted hetero [2 + 2] cycloaddition reactions are described here. This electron deficient variant of ynamine is more stable and easier to handle than most ynamines but possesses comparable reactivity. These reactions lead to a highly stereoselective synthesis of trisubstituted alkenes. A mechanistic model based on the stereochemical assignment is also described here. 10-Propynyl-9(10H)-acridone is also reactive toward α,β-unsaturated aldehydes and ketones. It provides hetero [2 + 2] products in reactions with α,β-unsaturated aldehydes but gives only the inverse demand [4 + 2] cycloadduct in a reaction with methyl vinyl ketone.

ChemInform Abstract: Regioselective Base‐Induced Condensations of Acrylic Acid Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Adsorption behavior and separation of vanadium(V), molybdenum(VI), and rhenium(VII) ions on crosslinked polymers containing acrylic acid derivative moieties

The radical polymerization of [2-(acryloyloxy)ethyl]trimethylammonium methyl sulfate and [3-(methacryloylamino)propyl]trimethylammonium chloride by using ammonium peroxydisulfate as initiator and N,N′-methylene-bis-acrylamide as crosslinker agent at 70°C for 17 h was carried out. The crosslinker agent in the feed ranged between 2 and 6 mol %. The resins were completely insoluble in water and characterized by elemental analysis and FTIR spectroscopy. The metal ion binding capacity of these resins with V(V), Mo(VI), and Re(VII) were investigated using the batch equilibrium type. The pH, but not the crosslinking percentage in the feed, influenced the retention capacity of the resin, particularly for V(V) and Re(VII). Thus, at pH 1 only < 15% of V(V) was retained, but at pH 3 higher than 97% of V(V) was adsorbed. The resin–ion equilibrium was achieved between 15 min and 2 h depending on the resin, ion, and crosslinking degree. According to the pH, it is possible separate Re(VII) and Mo(VI) from V(V) at pH 1.0. To reuse the resins, the ions were stripped by using HCl, H2SO4, and Na2CO3 at different concentrations. © 1999 John Wiley & Sons, Inc. J Appl Polym Sci 73: 369–376, 1999

ChemInform Abstract: Unusual [3 + 2] Cycloaddition of Acrylic Acid Derivatives to 7‐Formyl‐4,5,6,7‐tetrahydro‐4,5,7‐trimethylpyrrolo[3,2‐c]pyridine under Michael Reaction Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.