- N-acylation of ethanolamine using lipase: A chemoselective catalyst
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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
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- Comparison of the gelation behaviour of N-substituted tetradecanamide amphiphiles in organic liquids: Effect of hydrogen-bonding ability of the head-group
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In this work, we have investigated the role of intermolecular hydrogen-bonding (H-bonding) interaction of the head-groups of amphiphilic organogelators. For this we have designed, synthesized and studied the gelation behaviour of a series of amide amphiphiles having hydrocarbon chains with the same length (C14) but with -COOH, -OH, -NH2 or -N(CH 3)2) functionalities as head-group. These gelators, except the one with -N(CH3)2 head-group, efficiently gelated aromatic solvents. The gelation in all the solvents employed was observed to be thermoreversible. The gels were characterized by XRD spectroscopy, electron microscopy, and rheology. The amphiphiles were observed to form ribbon-like aggregates in aromatic solvents. The gel-to-sol transition temperatures as well as mechanical strengths of the organogels were observed to increase with the spacer length. The results suggest that the intermolecular H-bonding interactions between head-groups were essential for gelation.
- Pal, Amrita,Mahapatra, Rita Das,Dey, Joykrishna
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- Different roles for the acyl chain and the amine leaving group in the substrate selectivity of N-Acylethanolamine acid amidase
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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
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p. 1411 - 1423
(2021/07/17)
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- Methods for production of fatty acid alkanolamides (FAAAs) from microalgae biomass
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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)
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- Synthesis and biological activity of N-acyl O-indolylalkyl ethanolamines
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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
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experimental part
p. 768 - 770
(2011/11/13)
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- Synthesis and anticonvulsant activity of N-(2-hydroxyethyl)amide derivatives
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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
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experimental part
p. 34 - 40
(2009/06/18)
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- Synthesis of new plant growth regulator: N-(Fatty acid) O-aryloxyacetyl ethanolamine
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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
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p. 3231 - 3234
(2008/02/07)
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- USE OF CERTAIN N-ACYLETHANOLAMINES TO ACHIEVE ETHYLENE- AND CYTOKININ-LIKE EFFECTS IN PLANTS AND FUNGI
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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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