5863-78-5

Usage

Uses

Used in Organic Electronics:
(E)-3-(4-Methoxystyryl)pyridine is used as a material for organic light-emitting diodes (OLEDs) due to its favorable photophysical properties. Its ability to emit light under certain conditions makes it a valuable component in the development of advanced display technologies and energy-efficient lighting solutions.
Used in Optoelectronic Devices:
(E)-3-(4-Methoxystyryl)pyridine is also being explored for its potential applications in optoelectronic devices, which combine the functionalities of electronic and optical components. Its properties may contribute to the advancement of devices such as solar cells, photodetectors, and optical sensors.
Used as a Fluorescent Probe in Biological Imaging:
(E)-3-(4-Methoxystyryl)pyridine is being researched for its potential use as a fluorescent probe in biological imaging. Its ability to emit light when excited by a specific wavelength can be harnessed to visualize and study biological processes at the molecular level, aiding in the development of new diagnostic and therapeutic approaches in medicine.

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 626-55-1 3-Bromopyridine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 78-08-0 Triethoxyvinylsilane 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 637-69-4 4-Methoxystyrene 
• 99-96-7 4-hydroxy-benzoic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 121-98-2 methyl 4-methoxybenzoate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 1121-55-7 3-vinylpyridine 
• 500-22-1 3-pyridinecarboxaldehyde 

Downstream Products

• 879009-51-5 ethyl [4-[(E)-2-pyridin-3-ylvinyl]phenoxy]acetate 
• 85666-05-3 4-[(E)-2-(pyridin-3-yl)ethenyl]phenol 

Relevant academic research and scientific papers

A new insight into the push-pull effect of substituents via the stilbene-like model compounds

In this paper, authors report on 1-pyridyl-2-arylethenes, 1-furyl-2-arylethylenes, 1,2-diphenylpropylenes and substituted cinnamyl anilines as stilbene-like model compounds to investigate the factors dominating the push-pull effect of substituents via usi

Determination and application of the excited-state substituent constants of pyridyl and substituted phenyl groups

Thirty six 1-pyridyl-2-arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2-pyridyl, 3-pyridyl and 4-pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1-substituted phenyl-2-arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited-state substituent constants (Formula presented.) of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve-fitting method. Taking the λmax values of 358 samples of bi-arylethene derivatives as a data set and 126 samples of bi-aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained (Formula presented.) as a parameter, and good results were obtained for the two data sets. The reliability of the obtained (Formula presented.) values was verified. The results of this paper can provide excited-state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.

THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS

The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.

Inhibitory effect of cytotoxic nitrogen-containing heterocyclic stilbene analogues on VEGF protein secretion and VEGF, hTERT and c-Myc gene expression

A group of 21 nitrogen-containing heterocyclic stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity as well as their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non-tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and downregulate the expression of the VEGF, hTERT and c-Myc genes, of which the latter two are involved in controlling the activation of telomerase.

Heck cross-coupling of vinyl heteroaromatic compounds with aryl and heteroaryl halides using Pd(II) complex under phosphine-free conditions

The palladium-catalyzed cross-coupling reaction of vinyl heteroaromatic compounds with aryl bromides and heteroaryl bromides is described using air and moisture stable N,N′,N″,O-tetrafunctional Pd catalyst under phosphine-free conditions. As a result a variety of trans-1,2-disubstituted vinyl heterocycles were obtained in high to good yields.

Mechanistic studies on the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water: The effect of the solvent and NaOH promoter

The mechanism of the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water has been studied using different catalytic precursors. The NaOH promoter converts the initial vinylalkoxysilane into a highly reactive water-soluble vinylsilanolate species. Similarly, deuterium-labeling experiments have shown that, irrespective of the catalytic precursor used, vinylation occurs exclusively at the CH vinylic functionality via a Heck reaction and not at the C-Si bond via a Hiyama cross-coupling. The involvement of a Heck mechanism is interpreted in terms of the reduced nucleophilicity of the base in water, which disfavors the transmetalation step. The Heck product (β-silylvinylarene) undergoes partial desilylation, with formation of a vinylarene, by three different routes: (a) hydrolytic desilylation by the aqueous solvent (only at high temperature); (b) transmetalation of the silyl olefin on the PdH Heck intermediate followed by reductive elimination of vinylarene; (c) reinsertion of the silyl olefin into the PdH bond of the Heck intermediate followed by β-Si syn-elimination. Both the Hiyama and Heck catalytic cycles and desilylation mechanisms b and c have been computationally evaluated for the [Pd(en)Cl2] precursor in water as solvent. The calculated Gibbs energy barriers support the reinsertion route proposed on the basis of the experimental results.

Feeding the Heck reaction with alcohol: One-pot synthesis of stilbenes from aryl alcohols and bromides

Aryl alcohols are employed as feedstock for the Heck reaction. Keggin-type heteropolyacids catalyse the selective dehydration of the alcohols to styrenes, which, in one-pot, undergo palladium-catalysed Heck arylation with aryl bromides, affording broadly functionalised stilbenes. The choice of solvent is critical for the cascade dehydration-Heck reaction, with electron-rich aryl alcohols preferring a basic medium while electron-deficient ones demanding solvents of lower basicity. Copyright

Consecutive palladium-catalyzed Hiyama-Heck reactions in aqueous media under ligand-free conditions

Symmetric and asymmetric (E)-1,2-diarylethenes are synthesized from aryl bromides by consecutive one-pot Hiyama-Heck reactions carried out in water and under air; the only additives required are sodium hydroxide, palladium acetate and poly(ethylene glycol), and the products are isolable in many cases by simple filtration of the water solution. The Royal Society of Chemistry.

Substituted CIS- and trans-stilbenes as therapeutic agents

The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor kappaB

The transcription factor nuclear factor kappaB (NF-κB), which regulates expression of numerous antiinflammatory genes as well as genes that promote development of the prosurvival, antiapoptotic state is up-regulated in many cancer cells. The natural product resveratrol, a polyphenolic trans-stilbene, has numerous biological activities and is a known inhibitor of activation of NF-κB, which may account for some of its biological activities. Resveratrol exhibits activity against a wide variety of cancer cells and has demonstrated activity as a cancer chemopreventive against all stages, i.e., initiation, promotion, and progression. The biological activities of resveratrol are often ascribed to its antioxidant activity. Both antioxidant activity and biological activities of analogues of resveratrol depend upon the number and location of the hydroxy groups. In the present study, phenolic analogues of resveratrol and a series of substituted trans-stilbenes without hydroxy groups were compared with resveratrol for their abilities to inhibit the human tumor necrosis factor alpha-induced (TNF-α) activation of NF-κB, using the Panomics NF-κB stable reporter cell line 293/NF-κB-luc. A series of 75 compounds was screened to identify substituted trans-stilbenes that were more active than resveratrol. Dose-response studies of the most active compounds were carried out to obtain IC50 values. Numerous compounds were identified that were more active than resveratrol, including compounds that were devoid of hydroxy groups and were 100-fold more potent than resveratrol. The substituted trans-stilbenes that were potent inhibitors of the activation of NFκB generally did not exhibit antioxidant activity. The results from screening were confirmed using BV-2 microglial cells where resveratrol and analogues were shown to inhibit LPS-induced COX-2 expression.