129024-87-9

Usage

Uses

Used in Pharmaceutical Industry:
(4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide is used as a potential therapeutic agent for its possible involvement in various cellular processes. Its unique structure and properties may offer new avenues for the development of treatments targeting specific biological pathways.
Used in Research and Development:
In the field of research and development, (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide serves as a valuable compound for studying its structural and functional similarities to naturally occurring lipids. This can lead to a better understanding of cellular processes and the discovery of new therapeutic approaches.
Used in Cosmetics Industry:
Given its lipid-like nature, (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide may also find applications in the cosmetics industry, potentially being utilized in the development of skincare products that aim to mimic or enhance the skin's natural lipid barrier for improved hydration and protection.

Upstream product

• 645-31-8 3-hydroxytyramine hydrobromide 
• 98770-66-2 docosahexaenoic acid anhydride 
• 62-31-7 dopamine hydrochloride 
• 6217-54-5 docosahexaenoic acid 
• 1220710-22-4 2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-amine 
• 160801-26-3 N-hydroxysuccinimide DHA ester 
• 1220710-21-3 N-(2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethyl)-2,2,2-trifluoroacetamide 
• 1220710-18-8 Phth-dopamine(acetonide) 
• 57894-18-5 2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline 
• 65846-04-0 N-<2-(3,4-Dihydroxyphenyl)ethyl>trifluoracetamid 
• 51-61-6 dopamine 
• 1220710-23-5 DHA-dopamine(acetonide) 

Relevant academic research and scientific papers

Structure-Activity Relationships of Fish Oil Derivatives with Antiallergic Activity in Vitro and in Vivo

A series of unsaturated fatty acids in fish oil and their corresponding ethanolamide metabolites were explored to find active fish oil components of antiallergic activity in vitro. Ethanolamides of omega-3 fatty acids (α-linolenic acid, EPA, and DHA) were found to possess promising antiallergic activity, whereas free fatty acids and ethanolamides of other fatty acids exhibited no or weak potency. Based on this finding, structure-activity relationships of DHA-ethanolamide (DHEA) derivatives were investigated to yield better fatty acid derivatives with enhanced antiallergic activity in vitro and in vivo. When the ethanolamide moiety of DHEA was replaced by the substituted sulfonamide functionality, highly promising potency was provided in vitro. Compound 59 showed improved antiallergic activity in vivo over DHEA. The results indicate that optimized DHEA derivatives have enhanced antiallergic activity in vitro and in vivo, and the resulting structures will be an important basis for further development of bioavailable derivatives with promising allergy suppressive activity.

Method of synthesizing acetonide-protected catechol-containing compounds and intermediates produced therein

The inventors disclose here a novel, facile approach to the synthesis of acetonide-protected catechol-containing compounds having at least one amine group. In specific embodiments, the invention provides novel methods of synthesizing 3,4-dihydroxyphenylalanine (H-DOPA(acetonide)-OH (6)), Fmoc-protected H-DOPA(acetonide)-OH (Fmoc-DOPA(acetonide)-OH (7)), Fmoc-protected dopamine (Fmoc-dopamine(acetonide) (10)), TFA-protected dopamine (TFA-dopamine(acetonide) (13)) and acetonide-protected 4-(2-aminoethyl)benzene-1,2-diol (acetonide-protected dopamine (14)).

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.

Acetonide protection of dopamine for the synthesis of highly pure N-docosahexaenoyldopamine

Direct acetonide protection of the catechol of dopamine has proven to be problematic due to the formation of Pictet-Spengler isoquinolines. Here we report an efficient method for acetonide protection of dopamine, allowing the preparation of a dopamine prodrug without complications from the Pictet-Spengler reaction. Acetonide-protected dopamine was first synthesized by pre-protecting the amino group with phthaloyl followed by refluxing with 2,2-dimethoxypropane in the presence of TsOH. Further work demonstrated that Fmoc and trifluoroacetyl were also suitable N-protective groups, while Boc-protected dopamine gave an isoquinoline product. Acetonide-protected dopamine was coupled to DHA (all cis-4,7,10,13,16,19-docosahexaenoic acid) to produce the N-DHA-dopamine prodrug with high purity.

Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine

New amides of different fatty acids from the C18, C20, and C22 series with dopamine were synthesized. Pharmacological characterization in binding assays with rat brain membrane preparations and in the 'tetrad' of cannabinoid behavioral tests showed that, for these compounds, cannabinoid-like activity was dependent on the fatty acid moiety. Our data demonstrate that polyenoic fatty acid amides with dopamine comprise a new family of synthetic cannabimimetics.

N-docosahexaenoyl, 3 hydroxytyramine: A dopaminergic compound that penetrates the blood-brain barrier and suppresses appetite

Fatty acids with varying chain lengths (2-22 carbon atoms long) and degrees of unsaturation (0-6 double bonds) were used to synthesize dopaminergic compounds for a study of the carrier mediated transport of dopamine (DA) to the brain. The most active carrier was the all cis C22:6 fatty acid [docosahexaenoic acid,( DHA)]which increased DA uptake through the blood-brain barrier by greater than 7.5 fold. The DHA-DA compound, NMI 8739, depressed the general locomotor activity of mice in a dose dependent manner. It also suppressed the appetite of Balb c mice and Charles River rats by 50% and 95% respectively at a dose of 10 mg/kg. Daily administration of NMI-8739 for a three week period did not induce tolerance. These results demonstrate DHA's potential for the carrier mediated transport of small molecules to the brain.