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Acid Anhydride (acid + anhydride)
Selected AbstractsSynthesis of a New Seleninic Acid Anhydride and Mechanistic Studies into Its Glutathione Peroxidase ActivityCHEMISTRY - A EUROPEAN JOURNAL, Issue 23 2008Sun-Chol Yu Dr. Abstract Starting from low toxic salicyloylglycine, a new seleninic acid anhydride 7 that lacks Se,,,N or Se,,,O non-bonded interactions was synthesized. This compound exhibits a fourfold higher glutathione peroxidase-like (GPx-like) activity than ebselen and inhibits plant and mammalian 12/15-lipoxygenases at lower micromolar concentrations. Because of these pharmacological properties, 7 may constitute a new lead compound for the development of anti-inflammatory low-molecular-weight seleno-organic compounds. Analyzing the redox products of 7 with glutathione (GSH) and tBuOOH, we identified three potential catalytic cycles (A, B, C) of GPx-like activity that are interconnected by key metabolites. To study the relative contribution of these cycles to the catalytic activity, we prepared selected reaction intermediates and found that the activity of seleninic acid anhydride 7 and of the corresponding diselenide 11 and selenol 14 compounds were in the same range. In contrast, the GPx-like activity of monoselenide 9 was more than one order of magnitude lower. These data suggested that cycles A and B may constitute the major routes of GPx-like activity of 7, whereas cycle C may not significantly contribute to catalysis. [source] ChemInform Abstract: ipso-Acylation of 5,13-Di-tert-butyl-8,16-dimethyl[2.2]metacyclophane with Acid Anhydrides: Through-Space Electronic Interaction Among the Two Benzene Rings.CHEMINFORM, Issue 44 2009Tomoe Shimizu Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 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. [source] ChemInform Abstract: Synthesis of Symmetrical Carboxylic Acid Anhydrides from Acyl Chlorides in the Presence of In Metal and DMF.CHEMINFORM, Issue 28 2009Joong-Gon Kim Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 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. [source] Rhodium-Catalyzed Acylation of Vinylsilanes with Acid Anhydrides.CHEMINFORM, Issue 27 2005Motoki Yamane Abstract For Abstract see ChemInform Abstract in Full Text. [source] ChemInform Abstract: N-Acylation of Amides with Acid Anhydrides by Way of Dual Activation Using MgBr2×OEt2.CHEMINFORM, Issue 16 2002Shinji Yamada Abstract ChemInform 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. [source] "Tail,Tail Dimerization" of Ferrocene Amino Acid DerivativesEUROPEAN JOURNAL OF INORGANIC CHEMISTRY, Issue 25 2010Daniel Siebler Abstract Acid anhydrides of N-protected 1,-aminoferrocene-1-carboxylic acid (Fca) have been prepared and spectroscopically characterized (protection group Boc, Fmoc, Ac; 4a,4c). The structure of the Boc-derivative 4a has been determined by single-crystal X-ray crystallography. An intramolecular N,H···O hydrogen bond involving the carbamate units results in a ring structure containing the two ferrocene units, the anhydride moiety, and the hydrogen bond. In the crystal, the individual molecules are connected by intermolecular N,H···O hydrogen bonds of the carbamate unit. Experimental and theoretical studies suggest that the ring motif is also a dominant species in solution. Electronic communication across the anhydride moiety is found to be very weak as judged from electrochemical, spectroscopic, and theoretical experiments. [source] Hydrogenation/Regioselective C-Acylation Reaction of Diethyl Coumarin-3-phosphonate with NaBH4/Acid Anhydrides: A New One-Pot Tandem Reaction.CHEMINFORM, Issue 34 2006Nevena I. Petkova Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] Allergic contact dermatitis to copolymers in cosmetics , case report and review of the literatureCONTACT DERMATITIS, Issue 5 2006Sarah Quartier Copolymers or heteropolymers are large molecules with high molecular weights (>1000 D). They have been underestimated for a long time as to their sensitizing capacities. Allergic contact dermatitis to 6 copolymers in cosmetics and 1 in a medical dressing has been described; however, the nature of the hapten is still unknown. We report a case of allergic contact dermatitis to polyvinylpyrrolidone (PVP)/hexadecene copolymer in a purple-colored lipstick and review the literature on allergic contact dermatitis to 7 copolymers: PVP/hexadecene, PVP/eicosene, PVP/1-triacontene, methoxy polyethyleneglycol (PEG)-22/dodecyl glycols, methoxy PEG-17/dodecyl glycols, phthalic anhydride/trimellitic anhydride/glycols, and polyvinyl methyl/maleic acid anhydride. [source] Identification and quantification of in vitro adduct formation between protein reactive xenobiotics and a lysine-containing model peptideENVIRONMENTAL TOXICOLOGY, Issue 1 2003Peter Reichardt Abstract Formation of in vitro adducts between different classes of xenobiotics and the lysine-containing peptide Lys-Tyr was monitored by high-performance liquid chromatography and electrospray ionization mass spectrometry. The molecular structures of the main resulting products could be sensitively analyzed by mass spectrometry (flow injection analysis), enabling the detection of characteristic binding formations. Aldehydes such as formaldehyde, acetaldehyde, and benzaldehyde were shown to form stable linkages to lysine amino groups via Schiff bases. Other electrophilic substances (e.g., toluene-2,4-diisocyanate, 2,4-dinitro-1-fluorobenzene, 2,4,6-trinitrobenzene sulfonic acid, dansyl chloride, and phthalic acid anhydride) also formed covalent adducts with lysine residues. The reactivity of the compounds was quantified by measuring the amount of peptide that remained unchanged after incubation for a certain period with the xenobiotic. Although reactivity levels within this group of aldehydes varied only to a small extent, as would be expected, extreme differences were seen among the structurally heterogeneous group of nonaldehyde xenobiotics. These results support the hypothesis that simple chemical reactions may lead to the adduction of nucleophilic macromolecules such as peptides or proteins. Such reactions, in particular, Schiff base formation of aldehydes, have previously been shown to be capable of specifically interfering with costimulatory signaling on T cells. Our results suggest that electrophilic xenobiotics of other classes may also inherit the capacity to exert similar effects. Forming covalent linkage to peptides may represent a possible molecular mechanism of electrophilic xenobiotics in vivo, yielding immunotoxic effects. The model utilized in this study is appropriate for monitoring the adduction of xenobiotics to basic peptides and for analyzing the resulting molecular structures. © 2003 Wiley Periodicals, Inc. Environ Toxicol 18: 29,36, 2003. [source] The pH-dependent surface properties of gelatin-alkenylsuccinic acid anhydride derived surfactantsJOURNAL OF APPLIED POLYMER SCIENCE, Issue 6 2007Li-Huei Lin Abstract The pH-dependent surface properties of a gelatin,alkenylsuccinic acid anhydride derived surfactants, containing an oligopeptide residue and alkenyl groups, were studied. The surface properties examined included surface tension, contact angle, emulsifying power, and fluorescence properties. The results showed that the surface activities of gelatin derivatives and their detergent properties for T/W fabrics are improved at low pH. These improved features make gelatin-derived surfactants suitable for use as cleaning agents for lime-degradable substrates such as hair and wool. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007 [source] Some novel accelerating agents for nitroxide-mediated living free-radical polymerizationJOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 21 2005Huang Jianying Abstract Malononitrile (MN), trifluoroacetic acid anhydride, acetylacetone, acetoacetic ester, and diethyl malonate have been identified as novel rate-accelerating additives for nitroxide-mediated living free-radical polymerization. Among these additives, MN has the greatest accelerating effect. Adding MN at an MN/2,2,6,6-tetramethylpiperidine-oxyl (TEMPO) molar ratio of 4.0 results in a nearly 20 times higher rate of polymerization of styrene (St), and adding MN at an MN/TEMPO molar ratio of 2.5 results in a nearly 15 times higher rate of copolymerization of St and methyl methacrylate. The polymerization of St proceeds in a living fashion, as indicated by the increase in the molecular weight with time and conversion and the relatively low polydispersity. The polymerization rate of St is so quick that the conversion reaches 70% within 1 h at 125 °C when the molar ratio of MN to TEMPO is 4:1. Moreover, the reaction temperature can be reduced to 110 °C. A possible explanation for this effect is that the formation of hydrogen bonds between the MN and TEMPO moiety weakens the CON bond at the end of the polymer chain. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5246,5256, 2005 [source] Novel copolymers via nitroxide mediated controlled free radical polymerization of vinyl chlorideMACROMOLECULAR SYMPOSIA, Issue 1 2003Thomas Wannemacher Abstract Controlled free radical polymerization (CFRP) of vinyl chloride (VCM) and copolymerization with several comonomers have been studied in aqueous suspension. Therefore di-tert-butylnitroxide and three novel nitroxyl radicals were used as mediating agents. Copolymerization of VCM with styrene, partly combined with acrylonitrile, maleic acid anhydride and maleic acid imide as well as methyl methacrylate, n-butyl methacrylate, butyl acrylate and butadiene have been achieved, demonstrating an efficient route for novel vinyl chloride copolymer architecture. [source] Synthesis of a New Seleninic Acid Anhydride and Mechanistic Studies into Its Glutathione Peroxidase ActivityCHEMISTRY - A EUROPEAN JOURNAL, Issue 23 2008Sun-Chol Yu Dr. Abstract Starting from low toxic salicyloylglycine, a new seleninic acid anhydride 7 that lacks Se,,,N or Se,,,O non-bonded interactions was synthesized. This compound exhibits a fourfold higher glutathione peroxidase-like (GPx-like) activity than ebselen and inhibits plant and mammalian 12/15-lipoxygenases at lower micromolar concentrations. Because of these pharmacological properties, 7 may constitute a new lead compound for the development of anti-inflammatory low-molecular-weight seleno-organic compounds. Analyzing the redox products of 7 with glutathione (GSH) and tBuOOH, we identified three potential catalytic cycles (A, B, C) of GPx-like activity that are interconnected by key metabolites. To study the relative contribution of these cycles to the catalytic activity, we prepared selected reaction intermediates and found that the activity of seleninic acid anhydride 7 and of the corresponding diselenide 11 and selenol 14 compounds were in the same range. In contrast, the GPx-like activity of monoselenide 9 was more than one order of magnitude lower. These data suggested that cycles A and B may constitute the major routes of GPx-like activity of 7, whereas cycle C may not significantly contribute to catalysis. [source] Some biophysical properties of castor oil esterified with some acid anhydridesEUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, Issue 10 2008Mona A. Saied Abstract A series of castor oil adducts were synthesized by esterification of castor oil with acid anhydrides: phthalic, maleic and succinic anhydrides. The chemical structure of castor oil and the prepared adducts were characterized by means of IR and 1H,NMR spectroscopy. The number-average and weight-average molecular weights were measured by gel permeation chromatography. The electrical properties were studied through the permittivity, dielectric loss and conductivity measurements, which are considered to be in the range of electrical insulation. The electrical conductivity, which describes the ionic mobility of the systems, was found to be in the range of 10,9 to 10,12,S/cm. This indicates that castor oil and its esters could be used for antistatic applications. The viscosity,, and the activation energy,E,, obtained from the dependency of viscosity on temperature using the Arrhenius equation, were found to increase with increasing molecular weight of the system. The effect of different concentrations of castor oil and its esters on the growth activities of the sugar beet pathogens R.,solani and S.,rolfsii was studied through the determination of percent germination, average length of hyphal extensions, dry mass yield and the production of sclerotia. The obtained data indicate that the esterification of castor oil with anhydrides improves the antifungal activity. [source] Reinvestigation of the Mechanism of gem -Diacylation: Chemoselective Conversion of Aldehydes to Various gem -Diacylates and Their Cleavage under Acidic and Basic ConditionsEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 2 2005Veerababurao Kavala Abstract The mechanism of gem -diacylate formation has been studied extensively using tetrabutylammonium tribromide (TBATB) as the catalyst. The reaction proceeds by a nucleophilic attack of an anhydride on an aldehydic carbonyl group, nucleophilic attack of the hemiacylate intermediate on a second molecule of the anhydride, followed by an intermolecular attack of a second acetate group to regenerate the anhydride. gem -Diacylates of various aliphatic and aromatic aldehydes were obtained directly from the reaction of a variety of aliphatic and aromatic acid anhydrides in the presence of a catalytic quantity of tetrabutylammonium tribromide (TBATB) under solvent-free conditions. A significant electronic effect was observed during its formation as well as deprotection to the corresponding aldehyde. Chemoselective gem -diacylation of the aromatic aldehyde containing an electron-donating group has been achieved in the presence of an aldehyde containing an electron-withdrawing group. Deprotection of the gem -diacylate to the parent carbonyl compound can be accomplished in methanol in presence of the same catalyst. Here again, chemoselective deprotection of the gem -diacylate of a substrate containing an electrondonating group has been achieved in the presence of a substrate containing an electron-withdrawing group. Both the acid and base stability order of the various gem -diacylates examined follow a similar order. The stability order determined from the present study is: gem -dibenzoate > gemdipivalate > gem -diisobutyrate > gem -diacetate > gem -dipropionate. All the gem -diacylals are more stable under basic conditions than acidic condition. No correlation was found between the stability order and the pKa's of the corresponding acids; rather, the stability order is directly related to the steric crowding around the carbonyl carbon. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005) [source] Polycondensation of lactic acid catalyzed by organic acid anhydridesPOLYMER INTERNATIONAL, Issue 10 2007Yanbin Bai Abstract Poly(lactic acid) was prepared by the utilization of the acid anhydrides cis -butenedoic anhydride, phthalic anhydride and pyromellitic dianhydride as catalysts. The effect of the amount of catalyst, temperature and reaction time on the polymerization was investigated in detail. The results show that the acid anhydride catalysts are very efficient in bulk polycondensation, giving poly(D,L -lactic acid) with average molecular weights (Mw) of (1.7,2.3) × 104 in high yield. Copyright © 2007 Society of Chemical Industry [source] | |||||||||||||