- Pharmaceuticals and Surfactants from Alga-Derived Feedstock: Amidation of Fatty Acids and Their Derivatives with Amino Alcohols
-
Amidation of renewable feedstocks, such as fatty acids, esters, and Chlorella alga based biodiesel, was demonstrated with zeolites and mesoporous materials as catalysts and ethanolamine, alaninol, and leucinol. The last two can be derived from amino acids present in alga. The main products were fatty alkanol amides and the corresponding ester amines, as confirmed by NMR and IR spectroscopy. Thermal amidation of technical-grade oleic acid and stearic acid at 180°C with ethanolamine were non-negligible; both gave 61% conversion. In the amidation of stearic acid with ethanolamine, the conversion over H-Beta-150 was 80% after 3 h, whereas only 63% conversion was achieved for oleic acid; this shows that a microporous catalyst is not suitable for this acid and exhibits a wrinkled conformation. The highest selectivity to stearoyl ethanolamide of 92% was achieved with mildly acidic H-MCM-41 at 70% conversion in 3 h at 180°C. Highly acidic catalysts favored the formation of the ester amine, whereas the amide was obtained with a catalyst that exhibited an optimum acidity. The conversion levels achieved with different fatty acids in the range C12-C18 were similar; this shows that the fatty acid length does not affect the amidation rate. The amidation of methyl palmitate and biodiesel gave low conversions over an acidic catalyst, which suggested that the reaction mechanism in the amidation of esters was different. Pores versus acidity: The structures and properties of zeolites and mesoporous materials are investigated as catalysts for the amidation of renewable feedstocks, such as fatty acids, esters, and Chlorella alga based biodiesel, with ethanolamine, alaninol, and leucinol as nitrogen sources.
- Tkacheva, Anastasia,Dosmagambetova, Inkar,Chapellier, Yann,M?ki-Arvela, P?ivi,Hachemi, Imane,Savela, Risto,Leino, Reko,Viegas, Carolina,Kumar, Narendra,Er?nen, Kari,Hemming, Jarl,Smeds, Annika,Murzin, Dmitry Yu.
-
-
Read Online
- Optimized synthesis and characterization of N-acylethanolamines and O-acylethanolamines, important family of lipid-signalling molecules
-
The endocannabinoid anandamide (N-arachidonoylethanolamine, AEA), a physiologically occurring bioactive compound on CB1 and CB2 receptors, has multiple physiological functions. Since the discovery of AEA additional non-cannabinoid endogenous compounds such as N-palmitoylethanolamine (PEA), and N-oleoylethanolamine (OEA) have been identified from mammalian tissues. Virodhamine (O-arachidonoylethanolamine, VA) is the only identified new member of the endocannabinoid family that is characterised by an ester linkage between acylic acid and ethanolamine instead of the amide linkage found in AEA and others non-cannabinoid N-acylethanolamines. It has been reported, as a cautionary note for lipid analyses, that VA can be produced nonenzymatically from AEA (and vice versa) as consequence of O,N-acyl migrations. O,N-acyl migrations are well documented in synthetic organic chemistry literature, but are not well described or recognized with regard to methods in lipid isolation or lipid enzyme studies. We here report an economical and effective protocol for large scale synthesis and characterization of some N- and O-acylethanolamines that could be useful as reference standards in order to investigate their possible formation in biological membranes, with potentially interesting biological properties.
- Ottria, Roberta,Casati, Silvana,Ciuffreda, Pierangela
-
-
Read Online
- Polymorphism of N-stearoylethanolamine: Differential scanning calorimetric, vibrational spectroscopic (FTIR), and crystallographic studies
-
Based on a series of physicochemical properties (differential scanning calorimetry, powder X-ray crystallographic studies and Fourier-transform infra red spectroscopic analysis) determined for N-stearoylethanolamine (NSEA) (C18:0) at different temperatures, evidence has been given that this compound can exist in (at least) three polymorphic forms. Powder X-ray crystallography clearly demonstrates the presence of three distinct molecular packings at distinct temperatures while spectral changes in the vibrational spectra reveal that the geometry of the CH2-CO functional group of the molecule is affected during the polymorphic transitions. Rationalization of the thermal physicochemical behavior of NSEA in terms of molecular packing is also proposed. It supposes rearrangement of the hydrocarbon chains upon heating of the molecule.
- Wouters,Vandevoorde,Culot,Docquir,Lambert
-
-
Read Online
- Solvent-free “green” amidation of stearic acid for synthesis of biologically active alkylamides over iron supported heterogeneous catalysts
-
Stearoyl ethanolamine was synthesized by amidation of stearic acid with ethanolamine in solventless conditions. Iron containing heterogeneous catalysts supported on SiO2, Al2O3, Beta (BEA), ZSM-12 (MTW) and Ferrierite (FER) were used in this work. Sn-modified Ferrierite and H-Ferrierite were also studied for comparison. Fe-modified catalysts synthesized using solid state ion-exchange and evaporation impregnation methods, were thoroughly characterized with X-ray powder diffraction, scanning electron microscope, FTIR with pyridine, nitrogen adsorption, energy dispersive X-ray microanalysis and M?ssbauer spectroscopy. The highest conversion was obtained with Fe-H-FER-20 at 140?°C in 1?h giving 61% conversion and 98% selectivity towards the desired amide. The catalytic performance in terms of turnover frequency per mole of iron was achieved with the catalyst exhibiting the largest amount of Fe3+ species, optimum acidity and a relatively low Br?nsted to Lewis acid site ratio.
- M?ki-Arvela, P?ivi,Zhu, Jeanne,Kumar, Narendra,Er?nen, Kari,Aho, Atte,Linden, Johan,Salonen, Jarno,Peurla, Markus,Mazur, Anton,Matveev, Vladimir,Murzin, Dmitry Yu.
-
-
Read Online
- Structure and reactivity in langmuir films of amphiphilic alkyl and thio-alkyl esters of ?±-amino acids at the air/water interface
-
The structure and reactivity of alkyl esters of several ?±-amino acids self-assembled at the air/water interface have been investigated as part of our studies on mechanisms that are possibly relevant for the generation of homochiral prebiotic peptides. Grazing incidence X-ray diffraction (GIXD) studies of monolayers of racemic and enantiopure alkyl esters and thio-esters of alanine on the water surface demonstrated that these racemates self-assemble in the form of mixed solid solutions, because of disorder of the headgroups of the two enantiomers (enantiomeric disorder) within the two-dimensional (2D) crystallites. Matrix-assisted laser-desorption ionization time-of-flight Mass Spectrum (MALDI-TOF MS) analysis of the products collected from the air/water interface indicated the formation of low-molecular-weight oligopeptides (primarily dimers) and, in the case of some of the thioesters, small quantities of trimers and tetramers. Mass spectrometric studies on the diastereoisomeric distribution of the oligopeptides, starting from deuterium enantio-labeled monomers, demonstrated binomial statistics, such as that in reactions occurring in an isotropic environment. The alkyl esters of phenylalanine and tyrosine did not form 2D crystallites at the air/water interface, and, upon polycondensation, they yielded only dipeptides. The enantiomeric disorder within the 2D crystallites of the monomers of the alkyl esters and thioesters of racemic serine was absent. Polycondensation of these esters, however, yielded only dipeptides and tripeptides and they were not investigated further. In contrast to previous reports, the present studies demonstrate that this reaction does not proceed beyond the dipeptide stage and, therefore, cannot be regarded as a plausible system for the generation of prebiotic peptides.
- Eliash, Ran,Weissbuch, Isabelle,Weygand, Markus J.,Kjaer, Kristian,Leiserowitz, Leslie,Lahav, Meir
-
-
Read Online
- Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists
-
Abstract We recently reported that diphenylsilane structure can function as a cis-stilbene mimetic. Here, we investigate whether silyl functionality can also serve as a mimetic of aliphatic cis-olefin. We designed and synthesized various silyl derivatives of oleoylethanolamide (OEA: 8), an endogenous cis-olefin-containing PPARα agonist, and evaluated their PPARα/δ/γ agonistic activity. We found that diethylsilyl derivative 20 exhibited PPARα/δ agonistic activity, and we also obtained a PPARδ-selective agonist, 32. Our results suggest that incorporation of silyl functionality is a useful option for structural development of biologically active compounds.
- Kajita, Daisuke,Nakamura, Masaharu,Matsumoto, Yotaro,Ishikawa, Minoru,Hashimoto, Yuichi,Fujii, Shinya
-
-
Read Online
- Alkyl sulfonyl derivatized PAMAM-G2 dendrimers as nonviral gene delivery vectors with improved transfection efficiencies
-
Amphiphilic dendrimer-based gene delivery vectors bearing peripheral alkyl sulfonyl hydrophobic tails were constructed using low-generation PAMAM-G2 as the core and functionalized by means of the aza-Michael type addition of its primary amino groups to vinylsulfone derivatives as an efficient tool for surface engineering. While the unmodified PAMAM-G2 was unable to efficiently transfect eukaryotic cells, functionalized PAMAM-G2 dendrimers were able to bind DNA at low N/P ratios, protect DNA from digestion with DNase I and showed high transfection efficiencies and low cytotoxicity. Dendrimers with a C18 alkyl chain produced transfection efficiencies up to 3.1 fold higher than LipofectAMINE 2000 in CHO-k1 cells. The dendriplexes based in functionalized PAMAM-G2 also showed the ability to retain their transfection properties in the presence of serum and the ability to transfect different eukaryotic cell lines such as Neuro-2A and RAW 264.7. Taking advantage of the vinylsulfone chemistry, fluorescent PAMAM-G2 derivatives of these vectors were prepared as molecular probes to determine cellular uptake and internalization through a clathrin-independent mechanism.
- Morales-Sanfrutos, Julia,Megia-Fernandez, Alicia,Hernandez-Mateo, Fernando,Giron-Gonzalez, Ma Dolores,Salto-Gonzalez, Rafael,Santoyo-Gonzalez, Francisco
-
-
Read Online
- Synthesis and biological activity of N-acyl O-indolylalkyl ethanolamines
-
The plant-growth regulators, indole-3-carboxylic acids, were introduced into N-acyl ethanolamines, and a series of N-acyl O-indolylalkyl ethanolamines were prepared. Their biological activities to regulate rape hypocotyl elongation, cucumber cotyledon expansion and common wheat coleoptile growth were tested. The results indicate that the title compounds inhibited rape hypocotyl elongation, especially the indole-3-propionic acid derivatives, whose bioactivity was better than that of indole-3-acetic acid.
- Jiang, Shaoliang,Gao, Jianrong,Han, Liang
-
-
Read Online
- Different roles for the acyl chain and the amine leaving group in the substrate selectivity of N-Acylethanolamine acid amidase
-
N-acylethanolamine acid amidase (NAAA) is an N-terminal nucleophile (Ntn) hydrolase that catalyses the intracellular deactivation of the endogenous analgesic and anti-inflammatory agent palmitoylethanolamide (PEA). NAAA inhibitors counteract this process and exert marked therapeutic effects in animal models of pain, inflammation and neurodegeneration. While it is known that NAAA preferentially hydrolyses saturated fatty acid ethanolamides (FAEs), a detailed profile of the relationship between catalytic efficiency and fatty acid-chain length is still lacking. In this report, we combined enzymatic and molecular modelling approaches to determine the effects of acyl chain and polar head modifications on substrate recognition and hydrolysis by NAAA. The results show that, in both saturated and monounsaturated FAEs, the catalytic efficiency is strictly dependent upon fatty acyl chain length, whereas there is a wider tolerance for modifications of the polar heads. This relationship reflects the relative stability of enzyme-substrate complexes in molecular dynamics simulations.
- Ghidini, Andrea,Scalvini, Laura,Palese, Francesca,Lodola, Alessio,Mor, Marco,Piomelli, Daniele
-
p. 1411 - 1423
(2021/07/17)
-
- An Aldehyde Responsive, Cleavable Linker for Glucose Responsive Insulins
-
A glucose responsive insulin (GRI) that responds to changes in blood glucose concentrations has remained an elusive goal. Here we describe the development of glucose cleavable linkers based on hydrazone and thiazolidine structures. We developed linkers with low levels of spontaneous hydrolysis but increased level of hydrolysis with rising concentrations of glucose, which demonstrated their glucose responsiveness in vitro. Lipidated hydrazones and thiazolidines were conjugated to the LysB29 side-chain of HI by pH-controlled acylations providing GRIs with glucose responsiveness confirmed in vitro for thiazolidines. Clamp studies showed increased glucose infusion at hyperglycemic conditions for one GRI indicative of a true glucose response. The glucose responsive cleavable linker in these GRIs allow changes in glucose levels to drive the release of active insulin from a circulating depot. We have demonstrated an unprecedented, chemically responsive linker concept for biopharmaceuticals.
- Mannerstedt, Karin,Mishra, Narendra Kumar,Engholm, Ebbe,Lundh, Morten,Madsen, Charlotte S.,Pedersen, Philip J.,Le-Huu, Priska,Pedersen, S?ren L.,Buch-M?nson, Nina,Borgstr?m, Bj?rn,Brimert, Thomas,Fink, Lisbeth N.,Fosgerau, Keld,Vrang, Niels,Jensen, Knud J.
-
supporting information
p. 3166 - 3176
(2021/01/21)
-
- N-stearoylethanolamine — a new inhibitor of the hepatitis c virus reproduction
-
Aim. The study of the effect of endogenous cannabimimetic compound-N-stearoylethanolamine (NSE) on the hepatitis C virus (HCV) reproduction. Methods. The model of the surrogate HCV is a bovine diarrhea virus; cell culture model is cells transfected with cDNA of the human HCV and molecular docking has been used. Results. In vitro studies showed that NSE effectively inhibited the reproduction of a surrogate HCV in both MDBK cells and transfected Jurkat cells. Molecular docking suggested that NSE can bind to the active centers of both NS3 serine protease and HCV NS5B-polymerase and has an inhibitory effect on their activity. Conclusions. The obtained data confirm that using NSE is promising for the development of antiviral drug to suppress the HCV activity.
- Asmolkova, V. S.,Berdyshev, A. G.,Chumak, A. A.,Deryabin, O. M.,Dyadun, S. T.,Goridko, T. M.,Hula, N. M.,Kosiakova, G. V.,Meged’, O. F.,Porva, Yu. I.,Rybalko, S. L.,Starosyla, D. B.
-
p. 167 - 176
(2021/10/22)
-
- GLUCOSE-SENSITIVE PEPTIDE HORMONES
-
The present invention relates to a conjugate of the formula P-L-I, wherein P is a peptide hormone effecting the metabolism of carbohydrates in vivo, L is a hydrolysable linker molecule consisting of Lp and Lj, and I is a molecule capable of inhibiting the effect of the peptide hormone P on the metabolism of carbohydrates in vivo. Under in vivo conditions, the conjugate is the major compound. When the concentration of glucose increases in v/vo,the concentration of the peptide hormone effecting the metabolism of carbohydrates in vivo also increases.
- -
-
Page/Page column 33-34
(2020/01/11)
-
- A Convenient Protocol for the Synthesis of Fatty Acid Amides
-
Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.
- Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.
-
supporting information
p. 213 - 217
(2019/01/14)
-
- Improved fatty acid monoethanolamide synthesis method
-
The invention relates to an improved fatty acid monoethanolamide synthesis method, which comprises: 1) preparing a polystyrene resin containing a carboxyl activating agent; 2) carrying out a condensation reaction on the polystyrene resin obtained in the step (1) and fatty acid in the presence of a catalyst to obtain an immobilized active ester; and (3) in the presence of a solvent, carrying out a reaction on the immobilized active ester obtained in the step 2) and ethanolamine, carrying out simple filtration or centrifugation to remove the resin after completing the reaction, carrying out pressure reducing concentration on the obtained liquid phase, and carrying out vacuum drying to obtain the high-quality fatty acid monoethanolamide product. According to the present invention, the condensation reaction is performed under the normal temperature condition, the generation of the by-product is substantially reduced through the selection of the catalyst and the reaction parameters, and the yield of the reaction and the purity of the product are maximized; and with the synthesis method, the defects of more by-products, difficult purification and the like caused by unstable raw material, poor selectivity to ethanolamine and alkali high temperature condition in the prior art are overcome.
- -
-
Paragraph 0049-0053; 0059-0063
(2017/10/07)
-
- Fatty acid monoethanol amide succinate sulfonate and its preparation method and application
-
The invention provides a preparation method for fatty acid monoethanolamide succinate sulfonate. The preparation method is characterized by comprising the steps of generating amidation reaction by fatty acid and monoethanolamide to generate fatty acid monoethanolamide which is reacted with butenedioic acid or maleic anhydride to generate fatty acid monoethanolamide butenedioic acid ester, and generating salt formation reaction of the fatty acid monoethanolamide butenedioic acid ester and hydrosulphite to generate the fatty acid monoethanolamide succinate sulfonate. Compared with the prior art, trace cutting liquid prepared from the fatty acid monoethanolamide succinate sulfonate provided by the invention has high lubricating property, extreme pressure antiwear property and biological degradability; a high-end requirement on metal processing can be met only by using an extremely small amount of the trace cutting liquid; therefore, harm to the environment and workers is alleviated, and the pollution to the environment is reduced to the maximum extent.
- -
-
Paragraph 0063
(2016/11/24)
-
- A fatty acid monoethanol amide preparation method (by machine translation)
-
The invention discloses a fatty acid monoethanol amide preparation method, a fatty acid or a derivative thereof and a monoethanolamine according to a certain proportion, in the absence of solvent or mixed solvent system under full, add a certain amount of alkaline catalyst, under a certain temperature and stirring the reaction for a period of time, preparation of fatty acid monoethanolamine, this invention adopts the fatty acid or a derivative thereof as the amidation reaction preparation of fatty acid monoethanol amide of the acyl donor, has simple technological process, reaction efficiency. (by machine translation)
- -
-
Paragraph 0029; 0030
(2017/06/10)
-
- Antiproliferative activity of synthetic fatty acid amides from renewable resources
-
In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line - the most aggressive CNS cancer.
- Dos Santos, Daiane S.,Piovesan, Luciana A.,D'Oca, Caroline R. Montes,Hack, Carolina R. Lopes,Treptow, Tamara G.M.,Rodrigues, Marieli O.,Vendramini-Costa, Débora B.,Ruiz, Ana Lucia T.G.,De Carvalho, Jo?o Ernesto,D'Oca, Marcelo G. Montes
-
supporting information
p. 340 - 347
(2015/02/02)
-
- METHOD OF MAKING FATTY ACID N-ACYLALKANOLAMINES
-
The present invention relates to methods for making a fatty acid N-acylalkanolamine having the formula: One of the methods comprises the steps of providing a vinyl ester of a fatty acid having the formula: providing a primary or secondary alkanolamine having the formula: NHR1R2; and reacting the vinyl ester of the fatty acid with the alkanolamine under conditions effective to form the fatty acid N-acylalkanolamine. The other method comprises the steps of providing a fatty acid; purifying the fatty acid; providing a primary or secondary alkanolamine having the formula: NHR1R2; reacting the fatty acid with the alkanolamine under conditions effective to form the fatty acid N-acylalkanolamine; and purifying the formed fatty acid N-acylalkanolamine.
- -
-
Paragraph 0069-0074;0076-0082; 0096; 0098
(2013/11/19)
-
- An Improved method for synthesis of N-stearoyl and N-palmitoylethanolamine
-
Certain N-acylethanolamines interact with cannabinoid receptors and have anorexic and neuroprotective effects. Traditional methods for the synthesis of N-acylethanolamines use fatty acid chlorides, fatty acid methyl esters, free fatty acids and triacylgly
- Wang, Xiaosan,Wang, Tong,Wang, Xingguo
-
experimental part
p. 1305 - 1313
(2012/09/10)
-
- Synthesis and anticonvulsant activity of N-(2-hydroxyethyl)amide derivatives
-
A series novel of N-(2-hydroxyethyl)amide derivatives was synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, and their neurotoxicity was evaluated by the rotarod test (Tox). The maximal electroshock test showed that N-(2-hydroxyethyl)decanamide 1g, N-(2-hydroxyethyl)palmitamide 1l, and N-(2-hydroxyeth-yl)stearamide 1n were found to show a better anticonvulsant activity and also had lower toxicity than the marked anti-epileptic drug valproate. In the anti-MES potency test, these compounds exhibited median effective doses (ED50) of 22.0, 23.3, 20.5 mg/kg, respectively, and median toxicity doses (TD50) of 599.8, >1000, >1000 mg/kg, respectively, resulting in a protective index (PI) of 27.5, >42.9, >48.8, respectively. This is a much better protective index than that of the marked anti-epileptic drug valproate (PI = 1.6). To further investigate the effects of the anticonvulsant activity in several different models, compounds 1g, 1l, and 1n were tested having evoked convulsions with chemical substances, including pentylenetetrazloe, isoniazide, 3-mercaptopropionic acid, bicuculline, thiosemicarbazide, and strychnine.
- Guan, Li-Ping,Zhao, Dong-Hai,Xiu, Jing-Hui,Sui, Xin,Piao, Hu-Ri,Quan, Zhe-Shan
-
experimental part
p. 34 - 40
(2009/06/18)
-
- Highly efficient and stereoselective synthesis of β-glycolipids
-
β-Galactosylceramide and glycolipid analogues were prepared in high yield and with complete chemo and stereoselectivity by reaction of α-iodo glycosides with stannyl ceramides, formed in situ. TBAI was used to activate both the iodogalactose and the stannyl ether. The Royal Society of Chemistry 2008.
- Morales-Serna, Jose Antonio,Boutureira, Omar,Diaz, Yolanda,Matheu, M. Isabel,Castillon, Sergio
-
supporting information; experimental part
p. 443 - 446
(2008/10/09)
-
- Synthesis of new plant growth regulator: N-(Fatty acid) O-aryloxyacetyl ethanolamine
-
N-(Fatty acyl) O-aryloxyacetyl ethanolamines, prepared from N-acylethanolamine (NAE) and aryloxyacetic acid, were tested for plant growth regulating activity. Compared with N-stearoylethanolamine, most compounds exhibit improved plant growth stimulating activity. In particular, those with chlorine on aryl ring show better activity than 2,4-dichlorophenyloxyacetic acid in stimulating hypocotyls elongation of rape which indicates that chlorine on aryl ring appears significant. Moreover, these derivatives display improved solubility.
- Han, Liang,Gao, Jian-Rong,Li, Zheng-Ming,Zhang, Yun,Guo, Wei-Ming
-
p. 3231 - 3234
(2008/02/07)
-
- USE OF CERTAIN N-ACYLETHANOLAMINES TO ACHIEVE ETHYLENE- AND CYTOKININ-LIKE EFFECTS IN PLANTS AND FUNGI
-
N-acylethanolamines (NAEs) that can deliver an ethylene- or cytokinin-like effects to a plant, plant part or fungus are disclosed. Also disclosed are methods of using the NAES.
- -
-
-
- In Vitro Evaluation of Phosphocholine and Quaternary Ammonium Containing Lipids as Novel Anti-HIV Agents
-
A series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety was evaluated as potential anti-HIV-1 agents.Several analogues were identified as possessing activity with the most promising compound being rac-3-octadecanamido-2-ethoxypropylphosphocholine (8).Compound 8 exhibited an IC50 for the inhibition of plaque formation of 0.16 μM wich was 84-fold lower than the IC50 value determined for CEM-SS cell growth inhibition.Initial mechanistic studies have indicated that these compounds, unlike AZT, are not reverse transcriptase (RT) inhibitors, but instead appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production.Since these lipids are acting via a different mechanism, they represent an alternative approach to the chemotherapeutic treatment of AIDS as well as candidates for combination therapy with AZT.
- Meyer, Karen L.,Marasco, Canio J.,Morris-Natschke, Susan L.,Ishaq, Khalid S.,Piantadosi, Claude,Kucera, Louis S.
-
p. 1377 - 1383
(2007/10/02)
-
- Rapid Synthesis and Interconversions of Fatty 4,5-Dihydroimidazoles and Fatty 1,4,5,6-Tetrahydropyrimidines. Thermal Cyclizations of Fatty Amides Involving Phenyl Phosphorodiamidate
-
Brief heating of ethane-1,2- and propane-1,3-bis-fatty amides at 235-250 deg C with phenyl phosphorodiamidate gave routes to high yields of 2-fatty alkyl-4,5-dihydroimidazoles and 1,4,5,6-tetrahydropyrimidines.Ready interconversions of fatty dihydroimidazoles and tetrahydropyrimidines, involving diamine exchange with solvent, were observed on brief heating of these materials in ethylenediamine and trimethylenediamine as solvents.
- Butler, Richard N.,Thornton, John D.,O'Regan, C.B.
-
p. 2197 - 2200
(2007/10/02)
-
- Phenolic esteramide antioxidants
-
Novel phenolically substituted esterbisamides as antioxidants useful for the protection of organic materials such as synthetic and natural rubbers, plastics and petroleum products against oxidative degradation.
- -
-
-