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Acid Amides (acid + amide)
Kinds of Acid Amides Terms modified by Acid Amides Selected AbstractsConformationally Constrained ,-Amino Acid Derivatives by Intramolecular [2 + 2]-Photocycloaddition of a Tetronic Acid Amide and Subsequent Lactone Ring Opening.CHEMINFORM, Issue 14 2006Birte Basler 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] Synthesis, Cytotoxicity by Bioluminescence Inhibition, Antibacterial and Antifungal Activity of ([1,2,4]Triazolo[1,5- c]quinazolin-2-ylthio)carboxylic Acid AmidesARCHIV DER PHARMAZIE, Issue 11 2009Lyudmila N. Antipenko Abstract We report in this work the synthesis, cytotoxicity, and antimicrobial activity of ([1,2,4]triazolo[1,5- c]quinazolin-2-ylthio)carboxylic acid amides 4,7 in connection with our previous research in the preparation of triazoloquinazoline derivatives. Due to simplicity, general availability of starting materials, and high yields, the most reliable method of synthesis appeared to be the one with N,N -carbonyldiimidazole activation stage. The chemical structures of all obtained substances were deduced from FT-IR, 1H-NMR, EI-MS, and LC-MS spectral data. The results of cytotoxicity evaluated by bioluminescence inhibition of bacterium Photobacterium leiognathi, strain Sh1 showed that compounds 4.1, 4.6, and 6.1 were the most cytotoxic. Investigation of the antimicrobial and antifungal activity of amides 4,7 (concentration 5 mg/mL) was carried out by the stiff-plate agar-diffusion method. We found that the compounds possessed low (4.1, 4.7) antifungal activity against Candida tenuis and strong (4.21, 5.1, 5.9) or inefficient (4.7, 4.12, 4.16) activity against Aspergillus niger. Substances 5.1 and 5.9 slightly affected Mycobacterium luteum. Staphylococcus aureus was resistant to all obtained substances, and only the n -butyramide derivatives 7.1 and 7.5 inhibited the growth of Escherichia coli. Hence, there was no strong correlation between bioluminescence inhibition and antimicrobial activity of the investigated substances. [source] 4-Methyl-1,2,3-selenadiazole-5-carboxylic Acid Amides: Antitumor Action and Cytotoxic Effect Correlation.CHEMINFORM, Issue 40 2007Pavel Arsenyan 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] Substituted Pyrrolidine-2,4-dicarboxylic Acid Amides as Potent Dipeptidyl Peptidase IV Inhibitors.CHEMINFORM, Issue 38 2006Weir-Torn Jiaang 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] Non-Thiol Farnesyltransferase Inhibitors: N-(4-Aminoacylamino-3-benzoylphenyl)-3- [5-(4-nitrophenyl)-2-furyl]acrylic Acid Amides and Their Antimalarial Activity.CHEMINFORM, Issue 22 2005Katja Kettler Abstract For Abstract see ChemInform Abstract in Full Text. [source] ChemInform Abstract: Synthesis, Analgesic and Antiinflammatory Activity of ,-Acetoxyphenylacetic Acid Amides.CHEMINFORM, Issue 36 2001M. S. Mashevskaya 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] Synthesis of Fatty Acid Amides of Catechol Metabolites that Exhibit Antiobesity PropertiesCHEMMEDCHEM, Issue 10 2010Bruno Almeida Abstract A series of fatty acid amides of 3,4-methylenedioxymethamphetamine (MDMA) catechol metabolites were synthesized in order to evaluate their biological activities. Upon administration, all synthesized compounds resulted in negative modulation of food intake in rats. The most active compounds have affinity for the CB1 receptor and/or PPAR- ,; part of their biological activity may be caused by these double interactions. [source] Enantioselective Synthesis of Phospholenes via Asymmetric Organocatalytic Alkene IsomerizationADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 10 2008Lukas Hintermann Abstract An asymmetric synthesis of the 2,5-diphenylphosphol-2-ene fragment (,95% ee) has been realized via enantioselective Cinchona -alkaloid catalyzed double bond isomerization of a meso -2,5-diphenylphosphol-3-ene amide to a 2,5-diphenylphosphol-2-ene amide (up to 83% ee), followed by enantiomeric enrichment to ,95% ee by crystallization. The 2,5-diphenylphosphol-2-ene amide (a cyclic phosphinic acid amide) was hydrolyzed to the 2,5-diphenylphosphol-2-ene acid (a cyclic phosphinic acid) with retention of configuration at C-5. [source] Inheritance of resistance to carboxylic acid amide (CAA) fungicides in Plasmopara viticolaPLANT PATHOLOGY, Issue 2 2007U. Gisi Mandipropamid is a new mandelic acid amide fungicide expressing high activity against foliar infecting oomycetes, including the grapevine downy mildew, Plasmopara viticola. Because cross-resistance with the valinamide fungicides iprovalicarb and benthiavalicarb and the cinnamic acid amide fungicides dimethomorph and flumorph was postulated, all five compounds are classified as carboxylic acid amide (CAA) fungicides. To support this classification, cross-resistance among these compounds with field isolates and the segregation of resistance in F1 and F2 progeny of P. viticola were evaluated. A bimodal distribution of sensitivity in field isolates and cross-resistance among all CAAs for the vast majority of isolates were detected. Crosses between sensitive (s) and CAA-resistant (r) isolates of opposite mating types, P1 and P2, yielded abundant oospores. All F1 -progeny isolates were sensitive to CAAs (s:r segregation 1:0), whereas in F2 progeny segregation of about 9:1 (s:r) was observed suggesting that resistance to CAA fungicides is controlled by two recessive nuclear genes. Mating type segregated in a ratio P1:P2 of c. 2:1 in F1 and 1:1 in F2 progeny. In the same crosses, resistance to the phenylamide fungicide mefenoxam segregated in a ratio of c. 1:3:2 (sensitive:intermediate:resistant), reflecting the monogenic, semidominant nature of resistance. The risk of resistance in P. viticola was classified as high for phenylamide and moderate for CAA fungicides. This is the first report on the inheritance of phenotypic traits in P. viticola. [source] Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determinationRAPID COMMUNICATIONS IN MASS SPECTROMETRY, Issue 3 2006Maurizio Dalle Carbonare Fatty acid amides (FAAs), such as the N -acylamides, N -acylethanolamides, N -acyldopamines and N -acylamino acids, are now emerging as an important new class of lipid-signalling molecules. This paper provides evidence, based on high-performance liquid chromatography/electrospray ionisation mass spectrometry (HPLC/ESI-MS/MS), gas chromatography/mass spectrometry (GC/MS) and 1H-NMR, of the occurrence in mouse and bovine brain extracts of a compound characterised by a mass spectrum attributable to a FAA not previously described, namely, the isopropyl-amide of stearic acid (SIPA). A highly sensitive GC/MS method was developed for quantification of naturally occurring SIPA and, also, for purposes of comparison, that of palmitoylethanolamide (PEA), a structurally related compound commonly determined in animal tissues. The results obtained show that SIPA levels in mouse brain are 8,10-fold higher than those of PEA. Moreover, SIPA was found in human neuroblastoma cell (SHSY-5Y) extracts, at significantly higher levels following exposure of the cells to the mitochondrial inhibitor rotenone. All this evidence not only shows surprisingly that SIPA may be found naturally in mammalian biological extracts despite the unusual functional group (i.e. isopropylamide) implicated, but also raises many important questions concerning its biological origin. Copyright © 2005 John Wiley & Sons, Ltd. [source] Effect of phytate-removal and deamidation of soybean proteins on calcium absorption in the in situ ratsBIOFACTORS, Issue 1-4 2004Hitomi Kumagai Abstract Soybean proteins were deamidated by cation-exchange resins after phytate, the inhibitor for calcium absorption from the small intestine, was removed in order to provide the enhancement function of calcium absorption to soybean proteins. About 92% of the phosphorus was removed from the soybean proteins by anion-exchange-resin treatment, indicating that most of the phytate was removed. About 70% of the acid amide was deamidated by cation-exchange-resin treatment, and phytate-removed and deamidated soybean proteins (PrDS) having high calcium binding properties were obtained. PrDS were hydrolyzed by digestive enzymes and their calcium-binding properties and the enhancement function of the calcium absorption from the small intestine of rats were examined. As a result, PrDS retained their high calcium binding properties even after hydrolysis by digestive enzymes. in situ experiments showed that PrDS and their hydrolysates enhanced the calcium absorption from the intestine. [source] Determination of isokinetic ratios necessary for equimolar incorporation of carboxylic acids in the solid-phase synthesis of mixture-based combinatorial librariesBIOPOLYMERS, Issue 1 2002Achyuta N. Acharya Abstract The methods used to study the relative reaction rates of 45 different aliphatic and aromatic carboxylic acids when coupled to resin-bound amino acid amides is described. Competition experiments involving the coupling of incoming carboxylic acids to resin-bound amino acid amides were performed. The relative composition of each N-acylated amino acid amide in the resulting mixtures was compared to controls prepared by physically mixing equal aliquots of individual compounds in order to study the relative reaction rates of the incoming carboxylic acids. The ratios of the incoming carboxylic acids were then iteratively adjusted to yield as close to equimolar products as possible. As expected, the steric and electronic nature of the incoming carboxylic acids was found to influence their relative reaction rates. The steric hindrance of the resin-bound amino acid appears to have a proportional effect on the reaction rates of the incoming carboxylic acids. N-acylated amino acid amides in the final mixtures, prepared using the final isokinetic ratios, were found to be approximately equimolar. © 2002 Wiley Periodicals, Inc. Biopolymers 65: 32,39, 2002 [source] Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptorsBRITISH JOURNAL OF PHARMACOLOGY, Issue 2 2004James D Leggett The ability of the endogenous fatty acid amide, cis -oleamide (ODA), to bind to and activate cannabinoid CB1 and CB2 receptors was investigated. ODA competitively inhibited binding of the nonselective cannabinoid agonist [3H]CP55,940 and the selective CB1 antagonist [3H]SR141716A to rat whole-brain membranes with Ki values of 1.14 ,M (0.52,2.53 ,M, Hill slope=0.80, n=6) and 2.63 ,M (0.62,11.20 ,M, Hill slope=0.92, n=4), respectively. AEA inhibited [3H]CP55,940 binding in rat whole-brain membranes with a Ki of 428 nM (346,510 nM, Hill slope=,1.33, n=3). ODA competitively inhibited [3H]CP55,940 binding in human CB1 (hCB1) cell membranes with a Ki value of 8.13 ,M (4.97,13.32 ,M, n=2). In human CB2 transfected (hCB2) HEK-293T cell membranes, 100 ,M ODA produced only a partial (42.5±7%) inhibition of [3H]CP55,940 binding. ODA stimulated [35S]GTP,S binding in a concentration-dependent manner (EC50=1.64 ,M (0.29,9.32 ,M), R2=0.99, n=4,9), with maximal stimulation of 188±9% of basal at 100 ,M. AEA stimulated [35S]GTP,S binding with an EC50 of 10.43 ,M (4.45,24.42 ,M, R2=1.00, n=3, 195±4% of basal at 300 ,M). Trans -oleamide (trans- ODA) failed to significantly stimulate [35S]GTP,S binding at concentrations up to 100 ,M. ODA (10 ,M)-stimulated [35S]GTP,S binding was reversed by the selective CB1 antagonist SR141716A (IC50=2.11 nM (0.32,13.77 nM), R2=1.00, n=6). The anatomical distribution of ODA-stimulated [35S]GTP,S binding in rat brain sections was indistinguishable from that of HU210. Increases of similar magnitude were observed due to both agonists in the striatum, cortex, hippocampus and cerebellum. ODA (10 ,M) significantly inhibited forskolin-stimulated cyclic AMP (cAMP) accumulation in mouse neuroblastoma N1E 115 cells (P=0.02, n=11). ODA-mediated inhibition was completely reversed by 1 ,M SR141716A (P<0.001, n=11) and was also reversed by pretreatment with 300 ng ml,1 pertussis toxin (P<0.001, n=6). These data demonstrate that ODA is a full cannabinoid CB1 receptor agonist. Therefore, in addition to allosteric modulation of other receptors and possible entourage effects due to fatty acid amide hydrolase inhibition, the effects of ODA may be mediated directly via the CB1 receptor. British Journal of Pharmacology (2004) 141, 253,262. doi:10.1038/sj.bjp.0705607 [source] CE with electrochemical detection for investigation of label-free recognition of amino acid amides by guanine-rich DNA aptamersELECTROPHORESIS, Issue 17 2007Tao Li Abstract In this work, we report a simple and effective investigation into adaptive interactions between guanine-rich DNA aptamers and amino acid amides by CE with electrochemical (EC) detection. Argininamide (Arm) and tyrosinamide (Tym) were chosen as model molecules. On a copper electrode, Arm generated a good EC signal in 60 mM NaOH at 0.7 V (vs Ag/AgCl), while Tym was detected well on a platinum electrode at 1.3 V in 20 mM phosphate of pH 7.0. Based on their EC properties, the ligands themselves were used as indicators for the adaptive interactions investigated by CE-EC, making any step of labeling and/or modification of aptamers with indicators exempted. Hydrophilic ionic liquid was used as an additive in running buffer of CE to improve the sensitivity of Arm detection, whereas the additive was not used for Tym detection due to its negative effect. Two guanine-rich DNA aptamers were used for molecular recognition of Arm and Tym. When the aptamers were incubated with ligands, they bound the model molecules with high affinity and specificity, reflected by obvious decreases in the signals of ligands but no changes in those of the control molecules. However, the ligands were hardly affected by the control ssDNAs after incubation. The results revealed the specific recognition of Arm and Tym by the aptamers. The mechanisms for binding model molecules by aptamers were discussed. Not as expected, these aptamers were not to form the G-quartets, which were generally responsible for binding the ligands when the guanine-rich aptamers were used. [source] Denitrocyclization in synthesis of dibenzo[b,f][1,4]thiazepin-11(10h)-ones and their derivativesJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 6 2007Alexey V. Smirnov A convenient synthesis of the novel dibenzo[b,f][1,4]thiazepin-11(10H)-ones is reported. As a key step, the synthetic route includes intramolecular aromatic denitrocyclization of 2-(2,4-dinitro-phenylsulfanyl)-benzoic acid amides. Efficient procedures for denitrocyclization in the presence of different bases are developed. Reduction of the nitro group in the obtained heterocycles resulted in formation of primary amines, which were transformed into amides by acylation with different carboxylic acids. The synthesized compounds have a great potential of bioactivity and are useful objects for biomedicinal screening. [source] Tetrahedral intermediates in reactions of carboxylic acid derivatives with nucleophiles,JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, Issue 3 2005Martin Adler Abstract Transacylation reactions of carboxylic acids, carboxylic acid esters, carboxylic acid amides and other carboxylic acid derivatives are among the most widespread and most important reactions in chemistry and biochemistry. Already in 1887, Claisen suggested a tetrahedral intermediate in transformations of carboxylic acid derivatives with nucleophiles. A historical overview gives insight into the studies to detect possible tetrahedral intermediates in such reactions. However, only in recent years has detailed information concerning the structures of such species become available. In this review, neutral, cationic and anionic tetrahedral intermediates are described which serve as models for transacylations under neutral, acid-catalysed or basic conditions. The characteristically different structures correspond nicely with experimental experience with reactions of carboxylic acid derivatives and with quantum chemical model calculations on tetrahedral intermediates. Finally, by means of model calculations, an explanation is given for the fast reactions of Weinreb amides, RC(O)N(CH3)OCH3, with organolithium and even with Grignard reagents: the reactions are determined by comparatively stable chelate transition states. Copyright © 2004 John Wiley & Sons, Ltd. [source] N -Isopropyl enols of carboxylic acid amides,JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, Issue 8 2003Yi Xiong Lei Abstract Eight N -isopropyl compounds of the formal structure YY,CHCONHPr- i (6), Y,Y,,=,CO2Me, CO2CH2CF3, CN; YY,,=,Meldrum,s acid residue; Y,=,CO2Me, Y,,=,CO2CH2CF3, CN; Y,=,CO2CH2CF3, CO2CH(CF3)2, Y,,=,CN, and the N - t -butyl derivative of Meldrum's acid were prepared and their structures were investigated in the solid state and in solution. The x-ray diffraction data indicate that in the solid state the structure is that of the amide 6, when Y,=,Y,,=,CO2Me, whereas when Y,=,CO2Me, Y,,=,CN or YY,,=,Meldrum,s acid residue the structure is that of the enol (5) YY,C=C(OH)NHPr- i. The solid-state 13C spectra indicate structure 6 when Y,=,CO2Me, Y,,=,CO2R, R,=,Me, CH2CF3 and an enol structure for the other compounds studied. 1H, 13C and when available 19F NMR spectra showed that the enol/amide composition in solution is structure and solvent dependent, in analogy with the previously investigated N -Ph analogs. The percentage of enol (and KEnol) decrease in the order of solvents CCl4,>,CDCl3,>,THF- d8,>,CD3CN,>,DMSO- d6, DMF- d7. For Y,Y, the percentage of enol increases when the number of fluorine atoms in R of the CO2R increases, when CN replaces a CO2R group or for the cyclic Meldrum's acid derivative. Both E - and Z -enols were observed when Y,,,Y,, mostly at low temperature. The ,(OH) values increase with increased polarity of the medium and with increased strength of the hydrogen bonds in which they are involved. In THF- d8 and DMF- d7 the Z -enol/E -enol and the amide/enol ratios increase with increase in temperature. A main conclusion from the work is that the percentage of the enol increases, but not drastically, when the N -substituent is changed from Ph to i -Pr. Copyright © 2003 John Wiley & Sons, Ltd. [source] Extended application of a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid to the resolution of N -(substituted benzoyl)-,-amino acid amidesJOURNAL OF SEPARATION SCIENCE, JSS, Issue 10 2006Guanghui Tan Abstract A chiral stationary phase (CSP 1) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied to the resolution of N -(substituted benzoyl)-,-amino acid amides and esters. N -(Substituted benzoyl)-,-amino acid amides were well resolved using a mixture of acetic acid-triethylamine-acetonitrile (0.01 : 0.05 : 100, v/v/v) as an optimum mobile phase while N -(substituted benzoyl)-,-amino acid esters were not resolved at all. In contrast, both N -(substituted benzoyl)-,-amino acid amides and esters were not resolved at all or resolved very poorly on another CSP (CSP 2), which lacks the two N,H hydrogens of the amide tethers of CSP 1. Among the substituents on the benzoyl group of analytes, the nitro group was the best for good resolution of analytes on CSP 1. From these results, the two N,H hydrogens of the amide tethers of CSP 1, the carbonyl oxygen of the amide group of analytes, and the nitro group on the benzoyl group of analytes were concluded to play significant roles in chiral recognition. In addition, various N -(3,5-dinitrobenzoyl)leucine amides with different lengths of N -alkylamide chains were resolved on CSP 1 and N -(3,5-dinitrobenzoyl)leucine N -propylamide was found to show the best chiral recognition in terms of the separation (, = 1.30) and the resolution factor (RS = 3.17). [source] Deduced catalytic mechanism of d -amino acid amidase from Ochrobactrum anthropi SV3JOURNAL OF SYNCHROTRON RADIATION, Issue 3 2008Seiji Okazaki d -Amino acid amidase (DAA) from Ochrobactrum anthropi SV3 catalyzes d -stereospecific hydrolysis of amino acid amides. DAA has attracted attention as a catalyst for the stereospecific production of d -amino acids, although the mechanism that drives the reaction has not been clear. Previously, the structure of DAA was classified into two types, a substrate-bound state with an ordered , loop, and a ground state with a disordered , loop. Because the binding of the substrate facilitates ordering, this transition was regarded to be induced fit motion. The angles and distances of hydrogen bonds at Tyr149 O,, Ser60 O, and Lys63 N, revealed that Tyr149 O, donates an H atom to a water molecule in the substrate-bound state, and that Tyr149 O, donates an H atom to Ser60 O, or Lys63 N, in the ground state. Taking into consideration the locations of the H atoms of Tyr149 O,, Ser60 O, and Lys63 N,, a catalytic mechanism of DAA activity is presented, wherein a shift of an H atom at Tyr149 O, in the substrate-bound versus the ground state plays a significant role in the reaction. This mechanism explains well why acylation proceeds and deacylation does not proceed in the substrate-bound state. [source] PL03 Biochemistry and pharmacology of fatty acid amides , effects on inflammation, pain and pruritus and new perspectives in veterinary medicineJOURNAL OF VETERINARY PHARMACOLOGY & THERAPEUTICS, Issue 2006V. DI MARZO No abstract is available for this article. [source] Endocannabinoids and non-endocannabinoid fatty acid amides in cirrhosisLIVER INTERNATIONAL, Issue 6 2010Yang Ying-Ying No abstract is available for this article. [source] Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determinationRAPID COMMUNICATIONS IN MASS SPECTROMETRY, Issue 3 2006Maurizio Dalle Carbonare Fatty acid amides (FAAs), such as the N -acylamides, N -acylethanolamides, N -acyldopamines and N -acylamino acids, are now emerging as an important new class of lipid-signalling molecules. This paper provides evidence, based on high-performance liquid chromatography/electrospray ionisation mass spectrometry (HPLC/ESI-MS/MS), gas chromatography/mass spectrometry (GC/MS) and 1H-NMR, of the occurrence in mouse and bovine brain extracts of a compound characterised by a mass spectrum attributable to a FAA not previously described, namely, the isopropyl-amide of stearic acid (SIPA). A highly sensitive GC/MS method was developed for quantification of naturally occurring SIPA and, also, for purposes of comparison, that of palmitoylethanolamide (PEA), a structurally related compound commonly determined in animal tissues. The results obtained show that SIPA levels in mouse brain are 8,10-fold higher than those of PEA. Moreover, SIPA was found in human neuroblastoma cell (SHSY-5Y) extracts, at significantly higher levels following exposure of the cells to the mitochondrial inhibitor rotenone. All this evidence not only shows surprisingly that SIPA may be found naturally in mammalian biological extracts despite the unusual functional group (i.e. isopropylamide) implicated, but also raises many important questions concerning its biological origin. Copyright © 2005 John Wiley & Sons, Ltd. [source] Synthesis, Cytotoxicity by Bioluminescence Inhibition, Antibacterial and Antifungal Activity of ([1,2,4]Triazolo[1,5- c]quinazolin-2-ylthio)carboxylic Acid AmidesARCHIV DER PHARMAZIE, Issue 11 2009Lyudmila N. Antipenko Abstract We report in this work the synthesis, cytotoxicity, and antimicrobial activity of ([1,2,4]triazolo[1,5- c]quinazolin-2-ylthio)carboxylic acid amides 4,7 in connection with our previous research in the preparation of triazoloquinazoline derivatives. Due to simplicity, general availability of starting materials, and high yields, the most reliable method of synthesis appeared to be the one with N,N -carbonyldiimidazole activation stage. The chemical structures of all obtained substances were deduced from FT-IR, 1H-NMR, EI-MS, and LC-MS spectral data. The results of cytotoxicity evaluated by bioluminescence inhibition of bacterium Photobacterium leiognathi, strain Sh1 showed that compounds 4.1, 4.6, and 6.1 were the most cytotoxic. Investigation of the antimicrobial and antifungal activity of amides 4,7 (concentration 5 mg/mL) was carried out by the stiff-plate agar-diffusion method. We found that the compounds possessed low (4.1, 4.7) antifungal activity against Candida tenuis and strong (4.21, 5.1, 5.9) or inefficient (4.7, 4.12, 4.16) activity against Aspergillus niger. Substances 5.1 and 5.9 slightly affected Mycobacterium luteum. Staphylococcus aureus was resistant to all obtained substances, and only the n -butyramide derivatives 7.1 and 7.5 inhibited the growth of Escherichia coli. Hence, there was no strong correlation between bioluminescence inhibition and antimicrobial activity of the investigated substances. [source] Biosynthesis of fatty acid amide elicitors of plant volatiles by insect herbivores ,ARCHIVES OF INSECT BIOCHEMISTRY AND PHYSIOLOGY (ELECTRONIC), Issue 2 2005James H. Tumlinson Larvae of several species of Lepidoptera produce fatty acid amide elicitors that induce the plants on which they feed to synthesize and release volatile organic compounds. The volatiles released by the plants act as cues that aid in host location by natural enemies of the herbivorous larvae. The elicitors are synthesized in the larvae by enzymes embedded in the membranes of the crop and anterior midgut tissues. The fatty acid precursors of the elicitors are obtained from the plants on which the caterpillars feed, while the amino acid moieties appear to be obtained from pools within the insects. The fatty acid amide elicitors are rapidly hydrolyzed in the midgut and hindgut by enzymes in the gut lumen. The role of these fatty acid amides in caterpillar metabolism is not yet understood. Arch. Insect Biochem. Physiol. 58:54,68, 2005. © 2005 Wiley-Liss, Inc. [source] Urea interactions with protein groups: A volumetric study,BIOPOLYMERS, Issue 10 2010Soyoung Lee Abstract We determined the partial molar volumes and adiabatic compressibilities of N -acetyl amino acid amides, N -acetyl amino acid methylamides, N -acetyl amino acids, and short oligoglycines as a function of urea concentration. We analyze these data within the framework of a statistical thermodynamic formalism to determine the association constants for the reaction in which urea binds to the glycyl unit and each of the naturally occurring amino acid side chains replacing two waters of hydration. Our determined association constants, k, range from 0.04 to 0.39M. We derive a general equation that links k with changes in free energy, ,Gtr, accompanying the transfer of functional groups from water to urea. In this equation, ,Gtr is the sum of a change in the free energy of cavity formation, ,,GC, and the differential free energy of solute,solvent interactions, ,,GI, in urea and water. The observed range of affinity coefficients, k, corresponds to the values of ,,GI ranging from highly favorable to slightly unfavorable. Taken together, our data support a direct interaction model in which urea denatures a protein by concerted action via favorable interactions with a wide range of protein groups. Our derived equation linking k to ,Gtr suggests that ,,GI and, hence, the net transfer free energy, ,Gtr, are both strongly influenced by the concentration of a solute used in the experiment. We emphasize the need to exercise caution when two solutes differing in solubility are compared to determine the ,Gtr contribution of a particular functional group. © 2010 Wiley Periodicals, Inc. Biopolymers 93: 866,879, 2010. [source] Determination of isokinetic ratios necessary for equimolar incorporation of carboxylic acids in the solid-phase synthesis of mixture-based combinatorial librariesBIOPOLYMERS, Issue 1 2002Achyuta N. Acharya Abstract The methods used to study the relative reaction rates of 45 different aliphatic and aromatic carboxylic acids when coupled to resin-bound amino acid amides is described. Competition experiments involving the coupling of incoming carboxylic acids to resin-bound amino acid amides were performed. The relative composition of each N-acylated amino acid amide in the resulting mixtures was compared to controls prepared by physically mixing equal aliquots of individual compounds in order to study the relative reaction rates of the incoming carboxylic acids. The ratios of the incoming carboxylic acids were then iteratively adjusted to yield as close to equimolar products as possible. As expected, the steric and electronic nature of the incoming carboxylic acids was found to influence their relative reaction rates. The steric hindrance of the resin-bound amino acid appears to have a proportional effect on the reaction rates of the incoming carboxylic acids. N-acylated amino acid amides in the final mixtures, prepared using the final isokinetic ratios, were found to be approximately equimolar. © 2002 Wiley Periodicals, Inc. Biopolymers 65: 32,39, 2002 [source] GPR119, a novel G protein-coupled receptor target for the treatment of type 2 diabetes and obesityBRITISH JOURNAL OF PHARMACOLOGY, Issue S1 2008H A Overton GPR119 is a G protein-coupled receptor expressed predominantly in the pancreas (,-cells) and gastrointestinal tract (enteroendocrine cells) in humans. De-orphanization of GPR119 has revealed two classes of possible endogenous ligands, viz., phospholipids and fatty acid amides. Of these, oleoylethanolamide (OEA) is one of the most active ligands tested so far. This fatty acid ethanolamide is of particular interest because of its known effects of reducing food intake and body weight gain when administered to rodents. Agonists at the GPR119 receptor cause an increase in intracellular cAMP levels via G,s coupling to adenylate cyclase. In vitro studies have indicated a role for GPR119 in the modulation of insulin release by pancreatic ,-cells and of GLP-1 secretion by gut enteroendocrine cells. The effects of GPR119 agonists in animal models of diabetes and obesity are reviewed, and the potential value of such compounds in future therapies for these conditions is discussed. British Journal of Pharmacology (2008) 153, S76,S81; doi:10.1038/sj.bjp.0707529; published online 26 November 2007 [source] Synthesis of Fatty Acid Amides of Catechol Metabolites that Exhibit Antiobesity PropertiesCHEMMEDCHEM, Issue 10 2010Bruno Almeida Abstract A series of fatty acid amides of 3,4-methylenedioxymethamphetamine (MDMA) catechol metabolites were synthesized in order to evaluate their biological activities. Upon administration, all synthesized compounds resulted in negative modulation of food intake in rats. The most active compounds have affinity for the CB1 receptor and/or PPAR- ,; part of their biological activity may be caused by these double interactions. [source] Direct conversion of secondary phosphine oxides and H -phosphinates with [Di(acyloxy)iodo]benzenes to phosphinic and phosphonic amidesHETEROATOM CHEMISTRY, Issue 2 2009Anna Hubacz The reaction of [di(acyloxy)iodo]benzene with secondary phosphine oxides or H -phosphinates in the presence of primary or secondary amines allows one to obtain phosphinic or phosphonic acids amides in the one-pot process. We take advantage of the strong acylating system DAIB/R2P(O)H to phosphinylation of amines. However, the reaction mechanism is multipathway and causes yields of phosphinic or phosphonic acids amides to be moderate. When the concentration of amines is low, the intermolecular process plays a main role leading to the formation of carboxylic amides through mixed phosphoric,carboxylic anhydride, and also in the low concentration of amines, tetrahydrofuran effectively competes with the amines in the nucleophilic attack on the acylating intermediates. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:81,86, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20514 [source] | ||||||||||||||||||||||||||||