80715-09-9

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 100-39-0 benzyl bromide 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 872-85-5 pyridine-4-carbaldehyde 
• 667458-79-9 3,5-dimethoxybenzyl 3,5-bis(trifluoromethyl)phenyl sulfone 
• 98-03-3 thiophene-2-carbaldehyde 
• 498-60-2 furan-3-carboxaldehyde 
• 637-69-4 4-Methoxystyrene 
• 40243-87-6 3,5-dimethoxystyrene 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 33626-09-4 (E)-3,3',5,5'-tetrahydroxystilbene 
• 150258-79-0 (E)-1-<3,5-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 
• 80715-10-2 1-(3,5-dihydroxyphenyl)-2-(3,5-dihydroxyphenyl)ethane 
• 80715-11-3 3,5,3',5'-Tetraacetoxydiphenylethan 
• 125910-10-3 1,2-bis(3,5-dimethoxyphenyl)ethylene 
• 22976-41-6 3,5,3',5'-tetramethoxy-bibenzyl 
• 1182284-00-9 (E)-2-hydroxy-3,5,3′,5′-tetramethoxystilbene 
• 1325680-21-4 3,6-di(2-pyridyl)-4,5-di(3,5-dimethoxyphenyl)-1,4-dihydropyridazine 
• 1325680-08-7 3,6-di(2-pyridyl)-4,5-di-(3,5-dimethoxyphenyl)pyridazine 

Relevant academic research and scientific papers

Vinyl-Stilbene Compounds and Uses Thereof

The present invention relates to a biphenyl - stilbene (Vinyl-stilbene) - based compound and a pharmaceutical composition for preventing or treating norovirus infection comprising the same as an active ingredient. The present invention can be usefully used as a pharmaceutical composition for treating norovirus infection by showing superior norovirus inhibitory activity and lower cell toxicity as compared to previously known compounds.

Selenenate Anions (PhSeO?) as Organocatalyst: Synthesis of trans-Stilbenes and a PPV Derivative

The selenenate anion (RSeO?) is introduced as an active organocatalyst for the dehydrohalogen coupling of benzyl halides to form trans-stilbenes. It is shown that RSeO? is a more reactive catalyst than the previously reported sulfur analogues (sulfenate anion, RSO?) and selenolate anions (RSe?) in the aforementioned reaction. This catalytic system was also applied to the benzylic-chloromethyl-coupling polymerization (BCCP) of a bis-chloromethyl arene to form ppv (poly(p-phenylene vinylene))-type polymers with high yields, Mn (average molecular weight) up to 13,000 and ? (dispersity) of 1.15. (Figure presented.).

Photoinitiated carbonyl-metathesis: Deoxygenative reductive olefination of aromatic aldehydes: Via photoredox catalysis

Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the CC bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.

Identification of novel non-nucleoside vinyl-stilbene analogs as potent norovirus replication inhibitors with a potential host-targeting mechanism

Norovirus (NV), is the most common cause of acute gastroenteritis worldwide. To date, there is no specific anti-NV drug or vaccine to treat NV infections. In this study, we evaluated the inhibitory effect of different stilbene-based analogs on RNA genome replication of human NV (HNV) using a virus replicon-bearing cell line (HG23). Initial screening of our in-house chemical library against NV led to the identification of a hit containing stilbene scaffold 5 which on initial optimization gave us a vinyl stilbene compound 16c (EC50 = 4.4 μM). Herein we report our structure-activity relationship study of the novel series of vinyl stilbene analogs that inhibits viral RNA genome replication in a human NV-specific manner. Among these newly synthesized compounds, several amide derivatives of vinyl stilbenes exhibited potent anti-NV activity with EC50 values ranging from 1 to 2 μM. A trans-vinyl stilbenoid with an appended substituted piperazine amide (18k), exhibited potent anti-NV activity and also displayed favorable metabolic stability. Compound 18k demonstrated an excellent safety profile, the highest suppressive effect, and was selective for HNV replication via a viral RNA polymerase-independent manner. Its potential host-targeting antiviral mechanism was further supported by specific activation of heat shock factor 1-dependent stress-inducible pathway by 18k. These results suggest that 18k might be a promising lead compound for developing novel NV inhibitors with the novel antiviral mechanism.

One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes

The phospha-Peterson reaction between a lithiated secondary phosphane, MesP(Li)TMS, and an aldehyde affords Mes-phosphaalkenes which, upon methanol addition and P-oxidation, react with a second carbonyl compound site specifically to produce unsymmetric alkenes. The E/Z selectivity of the one-pot cross coupling is largely determined by the electronic nature of the aryl substituent of the first aldehyde, with electron-donating groups giving rise to increased amounts of Z-alkenes.

Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene

Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two-step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model-aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene. (Figure presented.).

Intramolecular energy transfer and photoisomerization in stilbene dendrimers

Stilbene dendrimers with energy harvesting chromophores, such as naphthalene and benzophenone, have been prepared and their photochemical and photophysical properties have been examined. These dendrimers underwent trans-cis mutual photoisomerization on excitation of the core stilbene or the peripheral naphthalene and benzophenone chromophores through several energy transfer processes, and photophysical processes such as intersystem crossing finally resulted in cis-trans isomerization of the core stilbene.

An effective Pd nanocatalyst in aqueous media: Stilbene synthesis by Mizoroki-Heck coupling reaction under microwave irradiation

Aqueous Mizoroki-Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h-1). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple product work-up make this protocol a great option for stilbene syntheses by Mizoroki-Heck reaction.

Convenient One-Step Synthesis of Benzo[c]phenanthridines by Three-Component Reactions of Isochromenylium Tetrafluoroborates and Stilbenes in Acetonitrile

A new type of three-component reaction of air-stable isochromenylium tetrafluoroborates with electron-rich stilbenes in acetonitrile has been developed under catalyst-free conditions in this work. This cascade multibond-formation reaction is initiated by an intermolecular oxa [4 + 2]-cycloaddition, relayed with a nucleophilic addition of acetonitrile, and terminated by an intramolecular Friedel-Crafts reaction, affording the corresponding benzo[c]phenanthridine analogues in one step.

Anticancer Evaluation of 3,4,5,4'-trans-tetramethoxystilbene (DMU-212) and Its Analogs Against an Extensive Panel of Human Tumor Cell Lines

DMU-212, a methoxylated resveratrol analog, has significant anticancer activity, and selectively targets tumor cells. A library of E-diarylstilbenes structurally related to DMU-212 has been synthesized and evaluated for anticancer activity against a large