- Synthesis of primary amides by lipase-catalyzed amidation of carboxylic acids with ammonium salts in an organic solvent
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The synthesis of butyramide and oleamide, by Candida antarctica lipase B-catalyzed amidation of the carboxylic acids, in an organic solvent with ammonium bicarbonate or ammonium carbamate as a source of ammonia results in good yields, making prior activation of the acids unnecessary.
- Litjens, Mike J. J.,Straathof, Adrie J. J.,Jongejan, Jaap A.,Heijnen, Joseph J.
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- Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex
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Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished by its high activity and selectivity, wide substrate scope and modest reaction conditions. A variety of primary amines, RCH2NH2 (R = aliphatic, aromatic and heteroaromatic), are converted to the corresponding amides using ambient air as an oxidant in the presence of a sub-stoichiometric amount of KOtBu in tBuOH. A set of control experiments, Hammett relationships, kinetic studies and DFT calculations are undertaken to divulge mechanistic details of the amine oxidation using 1. The catalytic reaction involves abstraction of two amine protons and two benzylic hydrogen atoms of the metal-bound primary amine by the oxo and hydroxo ligands, respectively. A β-hydride transfer step for the benzylic C-H bond cleavage is not supported by Hammett studies. The nitrile generated by the catalytic oxidation undergoes hydration to afford the amide as the final product. This journal is
- Yadav, Suman,Reshi, Noor U Din,Pal, Saikat,Bera, Jitendra K.
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p. 7018 - 7028
(2021/11/17)
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- Design, synthesis and gelation of low molecular weight organo-gelators derived from oleic acid via, amidation
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In recent decades, gels have been widely considered for various medicinal purposes and, in particular, wound healing applications. In this regard, amides of oleic acids and 9, 10-dihydroxyoctadecanoic acid are synthesized and characterized with the help of modern analytical tools. Among the mentioned amide frameworks, N-(2-aminoethyl)-oleamide exhibits high order of gelation not only with different organic solvents such as n-hexane and DMSO but also with different edible oils such as sesame oil, mustard oil, coconut oil and citriodora oil. Here, we briefly discuss the optimization of gelation conditions for the synthesized amides as organo-gelator, in addition to that the minimum gelation concentration and gelation temperature have also been studied.
- Gupta, Gaurav R.,Joshi, Narendra S.,Phalak, Raju P.,Waghulde, Govinda P.
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p. 1109 - 1116
(2021/11/17)
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- CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
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Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).
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Paragraph 0248
(2020/11/27)
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- A Convenient Protocol for the Synthesis of Fatty Acid Amides
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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.
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supporting information
p. 213 - 217
(2019/01/14)
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- A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides
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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
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supporting information
p. 375 - 381
(2018/02/07)
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- Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
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N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
- Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
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p. 3224 - 3230
(2018/04/23)
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- Method and apparatus for manufacturing carboxylic acid amide compound
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The present invention relates to a process and an apparatus for producing a carboxylic acid amide compound, and more particularly, to a process for producing a carboxylic acid amide compound which alternately performs a reaction process of a first manufacturing process that promotes the reaction between a first carboxylic acid and a first ammonia in the presence of a first catalyst and a reaction process of a second manufacturing process that promotes the reaction between a second carboxylic acid and a first ammonia in the presence of a second catalyst wherein each of them is progressed alternately between each preparation process so that the reaction between the carboxylic acid and the ammonia, which is intermittently carried out by the respective preparation processes, can be continuously performed, and moreover, the time required for the respective preparation processes is shortened, so that the carboxylic acid amide compound can be produced in a large amount in a short time.
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Paragraph 0059-0062; 0076
(2017/06/02)
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- Atmospheric synthetic method for oleic acid amide
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The invention discloses a normal pressure synthesis method of oleamide. The method comprises the following steps: (1) preparation of a solid acid catalyst, namely adding boric acid, phosphoric acid and phosphomolybdic acid to water, heating and stirring until the materials are dissolved, and filtering to obtain impregnation liquid; grinding a ZSM-5 molecular sieve, sieving, drying and cooling, impregnating in the impregnation liquid, filtering, drying and baking at high temperature to obtain the solid acid catalyst; and (2) catalytic synthesis of oleamide under normal pressure, namely conducting a synthesis reaction under normal pressure by taking oleic acid and urea as raw materials and the solid acid catalyst as a catalyst to obtain oleamide. According to the synthesis method disclosed by the invention, a novel solid acid catalyst is prepared, and the oleamide is prepared from oleic acid and urea through catalytic synthesis under normal pressure and not too high temperature; and the synthesis method is gentle in technological condition, safe, low in cost, favorable for industrial production and high in yield.
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Paragraph 0025; 0026
(2017/03/14)
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- A METHOD OF TREATING PERIPHERAL INFLAMMATORY DISEASE
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An active for use in the treatment or inhibition of an inflammatory disease associated with over-activation of Toll-like Receptor 4 (TLR4), Toll-like Receptor 2 (TLR2) and Myeloid differentiating protein 88 (Myd88) adaptor-like protein (Mal) while maintaining a subject's ability to respond normally to a pathogen, in which the active is an oleamide or a derivative thereof.
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Paragraph 0075-0077
(2016/12/01)
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- Estolide compounds, estamide compounds, and lubricant compositions containing the same
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Provided herein are compounds of the formula: wherein m is an integer greater than or equal to 1; n is an integer greater than or equal to 0; Z is selected from NR5, S, and O; Z′ is, independently for each occurrence, selected from NR5, S, and O; R1 is, independently for each occurrence, is an optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R5 is, independently for each occurrence, selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R3 and R4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Also provided are compositions containing the compounds and methods of making both the compounds and compositions thereof.
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Page/Page column 26
(2015/11/24)
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- Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
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Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 μM).
- Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.
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p. 5188 - 5197
(2013/09/02)
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- Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides
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Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.
- Divito, Erin B.,Davic, Andrew P.,Johnson, Mitchell E.,Cascio, Michael
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p. 2388 - 2394
(2012/07/27)
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- Vernonia oil: Conversion to a mixture of tertiary amines including N,N-Dimethyl-(12S,13R)-Epoxy-cis-9-Octadecenyl amine
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Vernonia galamensis is a new potential industrial oilseed crop found in tropical Africa. It is the source of a naturally epoxidized oil called vernonia oil (VO) which is extracted from the seed of the plant. In this study VO was used as the starting material for the synthesis of a mixture of amines, with the major product amine being N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine. VO was transesterified via a base catalyzed methanolysis using sodium methoxide to yield VO methyl esters (VOME). Aminolysis of the VOME with dimethylamine as reagent and solvent under reflux conditions afforded the tertiary amides, with N,N- dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide as the major product. The mixture was then subjected to metal hydride reduction with lithium aluminum hydride in diethylether under reflux conditions to obtain the desired amine mixture including N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine. Electron impact mass spectrometry was used to characterize the mixture of amines. Additionally, proton NMR, 13C NMR, and FTIR were used for characterization of N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine. To further confirm the conversion of VO to the amines, the quaternary ammonium salts were synthesized and characterized by matrix-assisted laser desorption ionization time-of-flight mass spectrometry.
- Johnson, Nikki S.,Ayorinde, Folahan O.
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experimental part
p. 1425 - 1430
(2011/11/11)
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- Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: A bioactive agent found in the essential oil of mountain celery seeds
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The unusual hypolipidemic activity of the methanolic fractionate of the essential oil (EOM) obtained from the mountain celery seed was previously reported. The most enriched 9(Z)-octadecenamide (oleamide) was speculated to be responsible for the relevant bioactivity. Chemically syntheized oleamide (CSO) yielded 85.1% with a purity of 98.6% when identified by RP-HPLC, FTIR, HREIMS, 1H NMR, and 13C NMR. CSO was tested for its antioxidative and hypolipidemic bioactivities. Results indicated CSO was potently hypolipidemic with regard to serum TG, TC, LDL-C, LDL-C/HDL-C, and hepatic TG (p 0.05), but not for serum HDL-C and hepatic TC. In addition, CSO exhibited only poor antioxidative activity, implicating the possibility that the hypolipidemic and antioxidative bioactivity of original EOM was due to another coexisting constituent, probably y-selinene. Conclusively, oleamide is a potent hypolipidemic agent as regarding its effects on decreasing serum TG, TC, LDL-C and hepatic TG.
- Cheng, Ming-Ching,Ker, Yaw-Bee,Yu, Tung-Hsi,Lin, L.I.-Yun,Peng, Robert Y.,Peng, Chiung-Huei
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experimental part
p. 1502 - 1508
(2010/09/09)
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- Process for the preparation of saturated or unsaturated primary fatty amines
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Process for the preparation of unsaturated and saturated primary fatty amines comprising the steps of chlorination, treatment by ammonia, reduction and purification
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Page/Page column 6-7
(2008/06/13)
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- A spectrophotometric assay for fatty acid amide hydrolase suitable for high-throughput screening
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Signalling via the endocannabinoids anandamide and 2-arachidonylglycerol appears to be terminated largely through the action of the enzyme fatty acid amide hydrolase (FAAH). In this report, we describe a simple spectrophotometric assay to detect FAAH activity in vitro using the ability of the enzyme to hydrolyze oleamide and measuring the resultant production of ammonia with a NADH/NAD+-coupled enzyme reaction. This dual-enzyme assay was used to determine Km and Vmax values of 104 μM and 5.7 nmol/min/mg protein, respectively, for rat liver FAAH-catalyzed oleamide hydrolysis. Inhibitor potency was determined with the resultant rank order of methyl arachidonyl fluorophosphonate > phenylmethylsulphonyl fluoride > anandamide. This assay system was also adapted for use in microtiter plates and its ability to detect a known inhibitor of FAAH demonstrated, highlighting its potential for use in high-throughput screening.
- De Bank, Paul A.,Kendall, David A.,Alexander, Stephen P.H.
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p. 1187 - 1193
(2007/10/03)
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- Process for the production of fatty acid amides
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This invention discloses a rapid method of production for fatty acid amide from fatty acid and urea. One example is the preparation of oleylamide from oleic acid and urea. The yields are high and oleylamide is selectively formed by judicious choice of catalyst. The production of fatty acid amide involves heating fatty acid and urea in a microwave oven with the use of Lewis acid catalyst. The product from the reaction is subjected to solvent extraction with chloroform and then followed by purification with n-hexane, ethanol and acetonitrile via recrystalisation method. Such an oleylamide is preferred for application as a mould release agent, slip agent in plastic film production, water repellent and as a raw material for cosmetics production.
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Page/Page column 3
(2008/06/13)
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- CONNEXIN 26 INHIBITORS AND CANCER METASTASIS INHIBITORS
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A connexin 26 inhibitor and a cancer metastasis inhibitor have a cis-oxirane structure and a terminal amide structure as represented by the following general formula (1): where R is a hydrogen atom or a hydrocarbon group, X is one of a hydrogen atom, a methansulfonyl group, an ethansulfonyl group, an acetyl group, a trifluoroacetyl group, a hydroxyl group, an alkoxy group and an amino group; m is an integer of from 4 to 10; and n is an integer of from 4 to 7..This compound is a novel cancer metastasis inhibitor which specifically inhibits the function of connexin 26.
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Page/Page column 8
(2008/06/13)
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- Acyl-CoA: Cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas
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Unsaturated fatty acid amides, 9(Z)-octadecenamide (2) and 9(Z),12(Z)-octadecadienamide (4) as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT) were isolated from the ethyl acetate extracts of the insect, Mylabris phalerate Pallas, and elucidated by their spectroscopic data analysis. Compounds 2 and 4 inhibited rat liver microsomal ACAT, hACAT-1, and hACAT-2 with IC50 values of 170, 85, and 63μM for 2 and of 151, 53, and 45μM for 4, respectively.
- Xu, Ming-Zhe,Lee, Woo Song,Kim, Mi Jeong,Park, Doo-Sang,Yu, Hana,Tian, Guan-Rong,Jeong, Tae-Sook,Park, Ho-Yong
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p. 4277 - 4280
(2007/10/03)
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- Fatty-acid amide hydrolase
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The soporific activity of cis-9,10-octadecenoamide and other soporific fatty acid primary amides is neutralized by hydrolysis in the presence of fatty-acid amide hydrolase (FAAH). Hydrolysis of cis-9,10-octadecenoamide by FAAH leads to the formation of oleic acid, a compound without soporific activity. FAAH has be isolated and the gene encoding FAAH has been cloned, sequenced, and used to express recombinant FAAH. Inhibitors of FAAH are disclosed to block the hydrolase activity.
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- Exploration of lipase-catalyzed direct amidation of free carboxylic acids with ammonia in organic solvents
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Lipase-catalyzed direct amidation of free carboxylic acids is possible with ammonia in organic solvents. For butyric acid as a model compound the reaction proceeds well despite precipitation of ammonium butyrate, provided that the added molar amounts of butyric acid and ammonia are in the same range. The addition of ammonium salts is a convenient way to ensure suitable ammonia concentrations. Using Candida antarctica lipase B as the biocatalyst, the amidation proceeds well for various carboxylic acids and is very enantioselective in the amidation of 4-methyloctanoic acid.
- Litjens, Mike J. J.,Straathof, Adrie J. J.,Jongejan, Jaap A.,Heijnen, Joseph J.
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p. 12411 - 12418
(2007/10/03)
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- Modulation of GABA(A) receptors and inhibitory synaptic currents by the endogenous CNS sleep regulator cis-9,10-octadecenoamide (cOA)
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1. Cis-9,10-octadecenoamide (cOA) accumulates in the CSF of sleep-deprived cats and may represent a novel signalling molecule. Synthetic cOA has been shown to induce physiological sleep when injected into laboratory rats. Here we assess the cellular mode of action of cOA in vitro. 2. In all rat cultured cortical neurones (pyramidal cells) examined, the synthetic brain lipid (3.2-64 μM) enhanced the responses to subsaturating GABA concentrations (up to circa 2x) in a concentration-dependent manner (EC50, circa 15 μM). 3. (20 μM) cOA significantly enhanced the affinity of exogenous GABA for its receptor without changing the Hill slope or the maximal response. These effects were not voltage-dependent or secondary to shifts in E(Cl). 4. In the absence of GABA, cOA directly evoked small inhibitory currents in a subpopulation (2 subunit was co-expressed with α1β2: the cOA response was not sensitive to the specific benzodiazepine antagonist flumazenil (1 μM). 8. cOA may represent an endogenous ligand for allosteric modulatory sites on isoforms of GABA(A) receptors which are crucial for the regulation of arousal and have recently been implicated in the circadian control of physiological sleep.
- Lees, George,Edwards, Michelle D.,Hassoni, Abdul A.,Ganellin, C. Robin,Galanakis, Dimitrious
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p. 873 - 882
(2008/04/18)
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- Method for sleep induction
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Sleep may be induced by administration of fatty acid primary amides, including cis-9,10-octadecenoamide. Furthermore, sleep deprivation may be assayed by analyzing cerebrospinal fluid with respect to the presence of fatty acid primary amides, including cis-9,10-octadecenoamide. The presence of cis-9,10-octadecenoamide in cerebrospinal fluid is correlated with comparative sleep deprivation.
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- Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): A synthetic approach to the chemical analysis of trace quantities of a natural product
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The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Δ-sleep-inducing peptide and prostaglandin D2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of sleep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.
- Cravatt, Benjamin F.,Lerner, Richard A.,Boger, Dale L.
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p. 580 - 590
(2007/10/03)
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- 9(Z)-Octadecenamide and Fatty Amides by Bacillus megaterium (B-3437) Conversion of Oleic Acid
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9(Z)-Octadecenamide, hexadecenamide, tetradecenamide and tetradecanamide were produced by a novel bioconversion of oleic acid with Bacillus megaterium NRRL B-3437.Although chemical synthesis is more practical, the bioconversion to fatty amides (5-7percent of total recovered lipids) was unique for its requirement of both enzymatic catalysis and equimolar oleic acid / ammonium salt substrates.Purified octadecenamide was obtained by silica gel and high-pressure liquid chromatographic procedures and was characterized by gas chromatography, mass spectrometry, infrared and nuclear magnetic resonance.KEY WORDS: Bacillus megaterium (B-3437), bioconversion, fatty amides, hexadecenamide, 9(Z)-octadecenamide, oleic acid.
- Kaneshiro, T.,Vesonder, R. F.,Peterson, R. E.,Weisleder, D.,Bagby, M. O.
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p. 491 - 494
(2007/10/02)
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- Reduction of Azides with Zinc Borohydride
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Zinc borohydride in 1,2-dimethoxyethane provides an efficient procedure for the reduction of organic azides.Aroyl, acyl, and arylsulfonyl azides readily undergo reduction at room temperatue to produce amides and sulfonamides in excellent yields; however, substitution with electron-withdrawing groups in the aroyl azides leads to the corresponding benzyl alcohols.Reduction of aryl and alkyl azides has also been achieved in high yields, under some modified conditions.
- Ranu, Brindaban C.,Sarkar, Arunkanti,Chakraborty, Rupak
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p. 4114 - 4116
(2007/10/02)
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- The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates
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Reaction of p-toluenesulphonyl cyanide or methanesulfonyl cyanide with carbon radicals, generated from the corresponding O-acyl-N-hydroxy-2-thiopyridone derivatives by visible light photolysis gives nitriles in good yield. The homolysis products of these sulfonyl nitriles can also be trapped by electron rich olefins. We have also found that carbon radicals react easily with mesyl or tosyl isothiocyanate producing thiocyanates.
- Barton,Jaszberenyi,Theodorakis
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p. 2613 - 2626
(2007/10/02)
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