cas 544-31-0, PALMITOYLETHANOLAMIDE | Articles data

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Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway
Anandamide (arachidonoylethanolamine, AEA), an endogenous agonist for both the cannabinoid CB, receptor and the vanilloid VR1 receptor, elicits neurobehavioral, anti-inflammatory, immunomodulatory, and proapoptotic effects. Because of the central role of nuclear factor-κB (NF-κB) in the inflammatory process and the immune response, we postulated that AEA might owe some of its effects to the suppression of NF-κB. This study shows that AEA inhibits tumor necrosis factor-α (TNFα)-induced NF-κB activation by direct inhibition of the IκB kinase (IKK)β and, to a lesser extent, the IKKα subunits of κB inhibitor (IκB) kinase complex, and that IKKs inhibition by AEA correlates with inhibition of IκBα degradation, NF-κB binding to DNA, and NF-κB-dependent transcription in TNFα-stimulated cells. AEA also prevents NF-κB-dependent reporter gene expression induced by mitogen-activated protein kinase kinase kinase and NF-κB-inducing kinase. The NF-κB inhibitory activity of AEA was independent of CB1 and CB2 activation in TNFα-stimulated 5.1 and A549 cell lines, which do not express vanilloid receptor 1, and was not mediated by hydrolytic products formed through the activity of the enzyme fatty acid amide hydrolase. Chemical modification markedly affected AEA inhibitory activity on NF-κB, suggesting rather narrow structure-activity relationships and the specific interaction with a molecular target. Substitution of the alkyl moiety with less saturated fatty acids generally reduced or abolished activity. However, replacement of the ethanolamine "head" with a vanillyl group led to potent inhibition of TNFα-induced NF-κB-dependent transcription. These findings provide new mechanistic insights into the anti-inflammatory and proapoptotic activities of AEA, and should foster the synthesis of improved analogs amenable to pharmaceutical development as anti-inflammatory agents.
Sancho, Rocio,Calzado, Marco A.,Di Marzo, Vincenzo,Appendino, Giovanni,Munoz, Eduardo
p. 429 - 438
(2003)
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Green aqueous-phase solvent-free high-purity synthesis method of palmitoylethanolamide
The invention discloses a green aqueous-phase solvent-free high-purity synthesis method of palmitoylethanolamide. The green aqueous-phase solvent-free high-purity synthesis method comprises the following steps: by taking food-grade palm oil as an initial raw material, carrying out high-pressure catalyst-free continuous hydrolysis reaction on the initial raw material in a high-temperature and high-pressure hydrolysis tower to obtain hydrolysate; and then rectifying the hydrolysate to obtain a high-purity compound palmitic acid A, and carrying out acylation reaction on the high-purity compound palmitic acid A and monoethanolamine to obtain high-puritypalmitoylethanolamide. According to the method, food-grade palm oil which is healthier and more friendly to human bodies is used as an initial raw material, a green water-phase solvent-free preparation method is adopted, side reactions and by-products are reduced, the product purity is greatly improved, meanwhile, no chemical solvent is used in the whole reaction section, the produced palmitoylethanolamidedoes not have any solvent residue, and the method is low in cost and suitable for industrial production.
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Paragraph 0033

(2021/05/12)

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)

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)

A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides
A green, one-pot approach based on the solvothermal amidation of carboxylic acids with amines has been developed for the synthesis of diverse aliphatic and aromatic amides. It does not require the use of catalysts or coupling reagents and it occurs in the presence of ethanol that has been proved to have a key role in the process. The proposed strategy is also extendable to biologically active amides and could represent a low-cost and waste-less alternative to the common synthetic pathways.
Dalu, Francesca,Scorciapino, Mariano A.,Cara, Claudio,Luridiana, Alberto,Musinu, Anna,Casu, Mariano,Secci, Francesco,Cannas, Carla
supporting information
p. 375 - 381
(2018/02/07)

Methods for production of fatty acid alkanolamides (FAAAs) from microalgae biomass
Provided herein are methods for fatty acid alkanolamide (FAAA) synthesis and isolation from lipid-containing algal biomass, and the products of such methods.
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Page/Page column 11; 12

(2017/02/28)

Design, synthesis and CoMFA studies of OEA derivatives as FAAH inhibitors
A total of 26 novel oleoylethanolamide derivatives were designed, synthesized, and characterized. All synthesized targets compounds were screened for their inhibitory activities against fatty acid amide hydrolase. Among of them, 13 compounds inhibit fatty acid amide hydrolase by 50% at the concentration of 100 μM. Of these compounds, the most active one is compound 9, which inhibit fatty acid amide hydrolase activity 98.35% at the concentration of 100 μM. Comparative molecular field analysis analyzes were performed based on obtained biological activities data and resulted in a statistically reliable comparative molecular field analysis model with high predictive abilities (r2 = 0.978, q2 = 0.613).
Han, Daxiong,Wang, Biyan,Jin, Hui,Wang, Haiyan,Chen, Meimei
p. 2951 - 2966
(2017/10/06)

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.
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Paragraph 0048-0052

(2017/10/07)

THERMAL ENERGY STORAGE AND TEMPERATURE STABILIZATION PHASE CHANGE MATERIALS COMPRISING ALKANOLAMIDES AND DIESTERS AND METHODS FOR MAKING AND USING THEM
This invention generally relates to thermoregulation and temperature stabilization, thermal protection and insulation, and nucleating agents. In particular, in alternative embodiments, provided are organic phase change materials comprising diesters and alkanolamides. In alternative embodiments, provided are Phase Change Material (PCMs) compositions comprising diesters and alkanolamides, and methods for making and using them. In alternative embodiments, the Phase Change Material (PCMs) compositions are used for thermal energy management, including energy storage and/or temperature stabilization, in various applications such as building, automotive, packaging, garment and footwear, textiles, fabrics, synthetic fibers, foods, microcapsules and other energy storage systems.
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Paragraph 0143; 0144

(2017/04/11)

CERAMIDE-LIKE FUNCTION IMPARTING AGENT
Provided are an agent for imparting ceramide-like function, an agent for reinforcing skin barrier function, a moisturizing agent and a skin drug for external use. The agent for imparting ceramide-like function comprises as an effective ingredient a derivative of succinic acid diamide represented by the following formula (1): [wherein R1 and R2 each independently represents a hydroxyalkyl group of from 1 to 6 carbon atoms, R3 represents a group: —CH2CH2CH2CH2—R4 or a group: —CH2CH═CHCH2—R4 (wherein R4 represents an alkyl group of from 8 to 26 carbon atoms)].
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Paragraph 0101; 0102; 0103; 0104; 0105

(2016/03/05)

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)
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Paragraph 0035; 0036

(2017/06/10)

Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α
A series of fatty acid amides were synthesized and their peroxisome proliferator-activated receptor α (PPAR-α) agonistic activities were evaluated in a normal rat liver cell line, clone 9. The mRNAs of the PPAR-α downstream genes, carnitine-palmitoyltransferase-1 and mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase, were determined by real-time reverse transcription-polymerase chain reaction (RT-PCR) as PPAR-α agonistic activities. We prepared nine oleic acid amides. Their PPAR-α agonistic activities were, in decreasing order, N-oleoylhistamine (OLHA), N-oleoylglycine, Oleamide, N-oleoyltyramine, N-oleoylsertonin, and Olvanil. The highest activity was found with OLHA. We prepared and evaluated nine N-acylhistamines (N-acyl-HAs). Of these, OLHA, C16:0-HA, and C18:1Δ9-trans-HA showed similar activity. Activity due to the different chain length of the saturated fatty acid peaked at C16:0-HA. The PPAR-α antagonist, GW6471, inhibited the induction of the PPAR-α downstream genes by OLHA and N-oleoylethanolamide (OEA). These data suggest that N-acyl-HAs could be considered new PPAR-α agonists.
Takao, Koichi,Noguchi, Kaori,Hashimoto, Yosuke,Shirahata, Akira,Sugita, Yoshiaki
p. 278 - 285
(2015/04/22)

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)

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.
p. 2670 - 2680
(2015/09/02)

N-ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE (NAAA) INHIBITORS AND THEIR USE THEREOF
A compound is represented as Formula I, a tautomer thereof, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. Compounds of Formula I are inhibitors of N-acylethanolamine hydrolyzing acid amidase (NAAA). The present technology is directed to compounds, compositions, and methods to inhibit N-acylethanolamine hydrolyzing acid amidase and to treat N-acylethanolamine hydrolyzing acid amidase mediated conditions in a subject.
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Paragraph 0137

(2015/12/08)

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.
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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)

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
p. 705 - 711
(2013/01/15)

Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 ～2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.
Dang, Hung The,Kang, Gyeoung Jin,Yoo, Eun Sook,Hong, Jongki,Choi, Jae Sue,Kim, Hyung Sik,Chung, Hae Young,Jung, Jee H.
experimental part
p. 1520 - 1527
(2011/03/23)

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
experimental part
p. 768 - 770
(2011/11/13)

Synthesis and antituberculosis activity of new fatty acid amides
This work reports the synthesis of new fatty acid amides from C16:0, 18:0, 18:1, 18:1 (OH), and 18:2 fatty acids families with cyclic and acyclic amines and demonstrate for the first time the activity of these compounds as antituberculosis agents against Mycobacterium tuberculosis H37Rv, M. tuberculosis rifampicin resistance (ATCC 35338), and M. tuberculosis isoniazid resistance (ATCC 35822). The fatty acid amides derivate from ricinoleic acid were the most potent one among a series of tested compounds, with a MIC 6.25 μg/mL for resistance strains.
D'Oca, Caroline Da Ros Montes,Coelho, Tatiane,Marinho, Tamara Germani,Hack, Carolina Rosa Lopes,Da Costa Duarte, Rodrigo,Da Silva, Pedro Almeida,D'Oca, Marcelo Gonalves Montes
scheme or table
p. 5255 - 5257
(2010/10/03)

N-acylation of ethanolamine using lipase: A chemoselective catalyst
The N-acylation of ethanolamine (2) with various fatty acids 1a-d and esters of fatty acids 1e-h using Candida antarctica B lipase (Novozym 435) are described and optimum conditions for selective N-acylation rather than O-acylation are also discussed. Microwave assisted solution phase, solid supported and conventional methods were investigated and results were compared. There is a synergy between the enzyme catalysis and microwave irradiation.
Kidwai, Mazaahir,Poddar, Roona,Mothsra, Poonam
experimental part

(2010/04/22)

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)

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)

AN IMPROVED PROCESS FOR THE SYNTHESIS OF PALMIDROL
The process of this invention comprises preparing anhydride of palmitic acid and alkyl or cycloalkyl haloformate by any conventional method, reacting anhydride so formed with ethnolamine in-situ, and isolating the product by any known methods such as solvent recovery or filtration followed by purifying the title product by recrystallization using organic solvents if so desired.
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Page/Page column 7-8

(2010/11/24)

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.
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Page 8

(2010/11/30)

Chemoselective N-acylation of amino alcohols promoted by magnesium oxide in aqueous organic solution
The reaction of hydrophilic amino alcohols with acid chlorides in the presence of magnesium oxide in aqueous organic solution (THF/H2O=4:1) cleanly provided alkanolamides.
Kim, Duck-Hee,Rho, Ho-Sik,You, Jae Won,Lee, Jong Chan
p. 277 - 279
(2007/10/03)

Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404
The biological actions of the endogenous cannabinoid anandamide are terminated by carrier-mediated transport into neurons and astrocytes, followed by enzymatic hydrolysis. Anandamide transport is inhibited by the compound N-(4-hydroxyphenyl)arachidonylamide (AM404). AM404 potentiates several responses elicited by administration of exogenous anandamide, suggesting that it may also protect endogenous anandamide from inactivation. To test this hypothesis, we studied the effects of AM404 on the plasma levels of anandamide using high-performance liquid chromatography/mass spectrometry (HPLC/MS). Systemic administration of AM404 (10 mg kg-1 intraperitoneal, i.p.) caused a gradual increase of anandamide in rat plasma, which was significantly different from untreated controls at 60 and 120 min after drug injection. In plasma, both AM404 and anandamide were associated with a plasma protein, which we identified as albumin by non-denaturing polyacrylamide gel electrophoresis. AM404 (10 mg kg-1, i.p.) caused a time-dependent decrease of motor activity, which was reversed by the cannabinoid CB1 receptor antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-me thyl-1H-pyrazole-3-carboxamide·hydrochloride (SR141716A, 0.5 mg kg-1, i.p). These results are consistent with the hypothesis that AM404 inhibits anandamide inactivation in vivo. (C) 2000 Elsevier Science B.V.
Giuffrida, Andrea,Rodriguez De Fonseca, Fernando,Nava, Felice,Loubet-Lescoulie, Patrick,Piomelli, Daniele
p. 161 - 168
(2007/10/03)

Use of N-acyl derivatives of aminoalcohols in the manufacture of a medicament for practicing neuroprotective action in neuropathological states connected with excitotoxicity
The use of N-acyl derivatives of aminoalcohols with mono- and di-carboxylic acids for the prevention and treatment of diseases connected with hyper and prolonged excitation by excitatory amino acids is described.
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(2008/06/13)

A Novel Technique for the Preparation of Secondary Fatty Amides. III. Alkanolamides, Diamides and Aralkylamides
A low-temperature synthesis of fatty alkanolamides, fatty diamides and fatty aralkylamides directly from triglycerides and primary amines provides essentially quantitative yields of the various products.The reactions run to completion in 3-12 h at temperatures of 50-60 deg C, approximately 100 deg C lower than employed in present conventional practice.The amines are used in excess and serve as solvent, reagent and, perhaps, as catalyst.The amides were characterized by melting point and spectroscopic (infrared and nuclear magnetic resonance) methods.If the mixed amides produced from the various natural triglyceride mixtures of fats and oils are acceptable products, this synthetic method provides these products in satisfactory quality while conserving energy and avoiding the intermediate production of free fatty acids or their esters. KEY WORDS: Alkanolamides, amidation, aralkylamides, diamides, methyl tallowate, palmitic acid, tallow, tripalmitin.
Feairheller, S. H.,Bistline, R. G.,Bilyk, A.,Dudley, R. L.,Kozempel, M. F.,Haas, M. J.
p. 863 - 866
(2007/10/02)

A synthesis of 2-substituted 2-aminoethanol derivatives having inhibitory activity against protein kinase C
A series of 2-aminoethanol derivatives was synthesized and their inhibitory activities against protein kinase C were investigated. Among these compounds, 2-endo-hexadecylamino-5-norbornene-2-exo-methanol (4h) and 2-endohexadecylamino-5-norbornene-2,3-exo-dimethanol (4i) inhibited protein kinase C at the IC50 values of 2 x 10-5 and 1 x 10-5 M, respectively, but not protein kinase A at a concentration of 1 x 10-3 M. The structure-activity relationships are discussed.
Iwasaki,Yamazaki,Nishitani,Kondo,Sato
p. 122 - 126
(2007/10/02)

Acyl Migration from Nitrogen to Oxygen with Triphenylphosphine-tetrahalogenomethane Reagent: Synthesis of Esters from 2-Amino Alcohols
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Dutta, Pradeep K.,Chaudhuri, Chandana,Mandal, Sukhendu B.,Banerjee, Ashis K.,Pakrashi, Satyesh C.,Achari, Basudeb
p. 2180 - 2188
(2007/10/02)

HIGH CHEMOSELECTIE SYNTHESIS OF CARBOXAMIDES BY USING SYN-PHENYLPYRIDYL-O-ACYL OXIMES(PPKO)
Various carboxamides are prepared chemoselectively in good yields by using syn-phenylpyridyl ketoxime(PPKO) as functional leaving group.
Miyasaka, Tadayo,Noguchi, Shunsaku
p. 701 - 704
(2007/10/02)

Monitored Aminolysis of 3-Acyl-1,3-thiazolidine-2-thiones: Synthesis of Amides and Amide Alkaloids
A functional heterocycle, 3-acyl-1,3-thiazolidine-2-thione has been shown to be effective as an acylating reagent for the amino group.ATT (1) was readily prepared by several methods, and reacted with various amino compounds in CHCl3, CH2Cl2, THF, EtOH, THF-H2O, or sulfolane to afford the corresponding amides, 2a-w and 3-10 in very high yields within a short time.This reagent exhibits high chemo-selectivity.Its reaction with the diamines 13 and 15 and the triamine 29, which include a primary amino group(s) and a secondary amino group, gave the products acylated only at the primary amino group(s), 14, 16, and 30, respectively, in high yields.Aminoalcohols and aminophenols were chemoselectively converted into acylaminoalcohols and acylaminophenols, respectively, by ATT (1).By utilizing this method, several amide alkaloids (26, 28, 30, and 34) were efficiently synthesized.This new aminolysis can be monitored by the disappearance of the yellow color of the starting materials, ATT (1); it is remarkably characteristic of this reaction. Keywords - monitored aminolysis; 3-acyl-1,3-thiazolidine-2-thione; high chemo-selectivity; amide synthesis; fagaramide; dolicotheline; spermidine; maytenine; N-ferulyltryptamine
Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadao,Takao, Sachiko,Fujita, Eiichi
p. 2687 - 2699
(2007/10/02)

MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE : A NEW CONVENIENT SYNTHESIS OF AMIDE
3-Acylthiazolidine-2-thiones (1) were easily prepared and they were treated with several amines in dichloromethane to give amides 4 in very high yields within a short time.Aminoalcohols and aminophenols were selectively converted into acylaminoalcohols and acylaminophenols, respectively, by this reaction.One can monitor the reaction by disappearance of the yellow color of the starting material 1.Some amide alkaloids (15-18) have effectively been synthesized.
Nagao, Yoshimitsu,Seno, Kaoru,Kawabata, Kohji,Miyasaka, Tadayo,Takao, Sachiko,Fujita, Eiichi
p. 841 - 844
(2007/10/02)