13487-46-2Relevant academic research and scientific papers
Synthesis of lysophosphatidylethanolamine analogs that inhibit renin activity
Turcotte,Yu,Lee,Pavanaram,Sen,Smeby
, p. 1184 - 1190 (1975)
A series of lysophosphatidylethanolamine analogs containing saturated and methylene interrupted cis olefinic fatty chains was synthesized by phosphorylation and phosphonylation of respective fatty alcohols. Arachidonyl and linolenyl phosphoryl ethanolamines, arachidonyl (2 phthalimidoethyl)phosphonate and arachidonyl (2 aminoethyl)phosphonate were found to be effective inhibitors of the renin renin substrate reaction in vitro; lysophosphatidylethanolamine analogs of lesser unsaturation were either weakly active or inactive. In a preliminary study, intramuscular administration of 25 mg/kg/day of arachidonyl (2 aminoethyl)phosphonate to the hypertensive rat caused pronounced reduction (50 mm) in blood pressure within 3 days; upon continued dosage (15 mg/kg/day) for an additional 4 days, plasma renin activity was found to be 16 ng/0.1 ml/15 hr as compared with 69 ng/0.1 ml/15 hr before initial drug administration. Arachidonic acid, arachidonyl alcohol, and several corresponding tetraenoid ester, amide, mesylate, and glyceryl ether derivatives, that are not phosphate or phosphonates esters, were found to exhibit negligible or modest inhibition of renin activity in vitro.
Synthesis and pharmacological evaluation of sulfamide-based analogues of anandamide
Cano, Carolina,Paez, Juan Antonio,Goya, Pilar,Serrano, Antonia,Pavon, Javier,Rodriguez de Fonseca, Fernando,Suardiaz, Margarita,Martin, Maria Isabel
, p. 4889 - 4895 (2009)
Arachidonyl and linoleyl sulfamide derivatives have been synthesized and their potential cannabimimetic properties evaluated in in vitro functional and binding assays. Replacement of the ethanolamide moiety of anandamide by -CH2NHSO2NH-R considerably reduces the CB1 receptor activity and only some of the compounds showed modest cannabinoid properties in binding assays. The new compounds were also tested as inhibitors of the FAAH enzyme but were inactive.
Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors
Segall, Yoffi,Quistad, Gary B.,Nomura, Daniel K.,Casida, John E.
, p. 3301 - 3303 (2003)
Arachidonylsulfonyl fluoride (3), reported here for the first time, is similar in potency to its known methyl arachidonylfluorophosphonate (2) analogue as an inhibitor of mouse brain fatty acid amide hydrolase activity (IC50 0.1 nM) and cannabinoid CB1 agonist [3H]CP 55,940 binding (IC50 304-530 nM). Interestingly, 3 is much more selective than 2 as an inhibitor for fatty acid amide hydrolase relative to acetylcholinesterase, butyrylcholinesterase and neuropathy target esterase. N-(2-Hydroxyethyl)arachidonylsulfonamide (4) is at least 2500-fold less potent than N-(2-hydroxyethyl)arachidonamide (anandamide) (1) at the CB1 agonist site.
Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches
Anderl, Felix,Balkenhohl, Moritz,Carreira, Erick M.,Fink, Moritz,Pfaff, Patrick
supporting information, p. 14495 - 14501 (2021/09/18)
We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates.In situdesilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermalZ-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.
FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS
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Page/Page column 82, (2019/06/23)
The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the β-position, and further comprising an α-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein R1, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.
LIPID COMPOUNDS AND COMPOSITIONS AND THEIR OPTHALMIC USE
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Page/Page column 63, (2017/07/23)
The invention relates to lipid compounds of formula (I) and their pharmaceutically acceptable salts for the prevention and/or treatment of ophthalmic disorders such as retinal degenerative disorders and ocular inflammatory diseases: (I) (wherein R1 is either a C9 to C22 alkyl group, or a C9 to C22 alkenyl group having from 1 to 6 double bonds; R2 is selected from the group consisting of a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, a carboxy group, an acyl group, an amino group, and an alkylamino group; R3 is a hydrogen atom, or a group R2; R4 is a carboxylic acid or a derivative thereof; and X is methylene (-CH2-), or an oxygen or sulfur atom).
METHODS FOR MODULATING IKS CHANNEL ACTIVITY
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Paragraph 00109, (2016/04/26)
Disclosed herein are methods of using polyunsaturated fatty acids and derivatives thereof ("PUFAs") to modulate Iks channels to treat conditions associated with a disruption in Iks channel activity, such as cardiac arrhythmias. In particular, disclosed herein are negatively charged PUFAs having decreased pKa values, which can activate (i.e., open) IKs channels, and positively charged PUFAs that can inhibit (i.e., close) IKS channels.
Synthesis of novel thiourethane analogs of neurolipins
Gretskaya,Druzhinina,Bobrov,Bezuglov
, p. 222 - 225 (2013/07/26)
Thiourethane analogs of anandamide and arachidonic acid amides with cyclopropylamine, dopamine, and serotonin that were capable of inhibiting hydrolysis of fatty-acid amides and interacting with cannabinoid receptor type 1 were synthesized for the first t
Spiralisones A-D: Acylphloroglucinol hemiketals from an Australian marine brown alga, Zonaria spiralis
Zhang, Hua,Xiao, Xue,Conte, Melissa M.,Khalil, Zeinab,Capon, Robert J.
, p. 9671 - 9676 (2013/01/16)
An intertidal sample of the Australian marine brown alga, Zonaria spiralis, exhibited promising kinase inhibitory and antibacterial activity. Chemical analysis returned six phloroglucinol-derived lipids, the new hemiketal spiralisones A-D (1-4) and the known chromones 5-6, and the known norsesquiterpenoid apo-9′-fucoxanthinone (7). Structures 1-7 were assigned on the basis of detailed spectroscopic analysis, biosynthetic considerations and total synthesis. Spiralisones undergo facile acid-mediated dehydration to yield the corresponding chromones, revealing for the first time that brown algal chromones may be handling artifacts rather than natural products. Hemiketals 1 and 2, and chromone 6, displayed inhibitory activity against the neurodegenerative disease kinase targets CDK5/p25, CK1δ and GSK3β, while hemiketals 1, 3 and 4, and chromone 6, displayed growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis (ATCC 6051 and 6633). The promising kinase inhibitory and antibacterial properties of the Z. spiralis extract were attributed to the cumulative effect of many moderately potent phloroglucinol-derived lipid co-metabolites. The Royal Society of Chemistry 2012.
Process for the Synthesis of Long-Chain Fatty Acids
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Page/Page column 35, (2011/05/08)
This invention relates to processes for preparing long-chain fatty acids of Formula I: and salts thereof, as well as intermediates for the processes, wherein L1 and L2 are described herein.
