83088-26-0

Usage

Chemical Properties

White crystalline powder

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 78055-65-9 diethyl (3,4-dimethoxybenzyl)phosphonate 
• 159386-47-7 diphenyl 3,4-dimethoxybenzylphosphine oxide 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 32507-66-7 isorhapontigenin 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 62502-00-5 3-hydroxy-4,3,5-trimethoxy-trans-stilbene 
• 500-65-2 rhapontigenin 
• 74-88-4 methyl iodide 
• 397333-50-5 (3,5-dimethoxy-benzyl)phosphonic acid dimethyl ester 
• 6380-23-0 3,4-dimethoxystyrene 
• 25245-27-6 1-iodo-3,5-dimethoxybenzene 

Downstream Products

• 22318-87-2 3,5,4',5'-tetramethoxydihydrostilbene 
• 134029-77-9 1-(4-acetamidophenyl)-2-(3,4,5-trimethoxyphenyl)ethane 
• 10083-24-6 trans-piceatannol 
• 22318-84-9 2,3,5,7-tetramethoxy-9,10-dihydrophenanthrene 
• 1182284-01-0 (E)-2-hydroxy-3,5,3′,4′-tetramethoxystilbene 

Relevant academic research and scientific papers

Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C-O Bond Cleavage

A new protocol has been developed for the borylation of conjugated alkenyl methyl ethers using B2Pin2 via C-O bond cleavage catalyzed by Ni(II). In this cross-coupling reaction, both E/Z isomers of alkenyl ethers are converted into (E)-alkenyl boronic esters with good reactivity. This transformation exhibits high chemoselectivity in the presence of competitive C-O bonds such as aryl ether, ester, amide, and thioether groups, thus providing a new method for the construction of various alkenyl boronates.

Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction

Abstract: Five different Ru metal precursors were reduced in imidazolium based ionic liquids under hydrogen atmosphere (4?bar) at 50 °C to obtain well-dispersed and stable Ru nanoparticles. Transmission electron microscopy (TEM) analysis confirmed size of well dispersed ionic liquid mediated Ru particles (Ru NPs) of 5?nm (±0.5) in diameter. These ruthenium nanoparticles (in ionic liquids) were used for Wittig type olefination reaction under mild reaction environment (70 °C and 1?h). The corresponding stilbenes were obtained in good yield with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212. Graphical Abstract: [Figure not available: see fulltext.]

Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition

A small library of polymethoxystilbene glycosides (20-25) related to the natural polyphenol resveratrol have been synthesized and subjected, together with their aglycones 17-19, to an antiproliferative activity bioassay toward Caco-2 and SH-SY5Y cancer cells. Six of the compounds exhibit antiproliferative activity against at least one cell line. In particular, compounds 17 and 18 proved highly active on at least one of the two cell cultures. Compound 18 showed a GI50 value of 3 ΜM against Caco-2 cells, a value comparable to that of the anticancer drug 5-fluorouracil. The closely related compound 19 proved inactive, and its conjugates 22 and 25 showed weak cell growth inhibition. The results indicate that minimal differences in the structure of both polymethoxystilbenes and their glycosides can substantially affect the antiproliferative activity. The possible hydrolytic release of the aglycones 17-19 by β-glucosidase or β-galactosidase was also evaluated. Compounds 20-25 were also tested as potential β-glucosidase, β-galactosidase, and α-glucosidase inhibitors. A promising inhibitory activity toward α-glucosidase was observed for 21 (IC50 = 78 ΜM) and 25 (IC50 = 70 ΜM), which might be indicative of their potential as lead compounds for development of antidiabetic or antiobesity agents.

Synthesis and biological evaluation of novel (E) stilbene-based antitumor agents

Several new (E) stilbenes were synthesized by a combination of a Wittig olefination followed by Mizoroki-Heck coupling reactions. These compounds were screened for antitumor activity in a panel of 8 human cancer cell lines by a colorimetric SRB assay. Several of these compounds exhibit strong cytotoxicity. The most active compound of this series showed an average IC50 value of 0.03 μmol; it acts by apoptosis as shown by a dye-exclusion test, an extra acridine orange/ethidium bromide staining and DNA-laddering experiments.

NOVEL PROCESS FOR THE SYNTHESIS OF (E)-STILBENE DERIVATIVES WHICH MAKES IT POSSIBLE TO OBTAIN RESVERATROL AND PICEATANNOL

A subject-matter of the present invention is a novel process for the synthesis of (E)- stilbene derivatives targeted at obtaining in particular resveratrol and piceatannol.

Stilbene derivatives and their use in medicaments

The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R1 to R6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and s

Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers

New carbon-11 and fluorine-18 labeled stilbene derivatives, cis-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]8a), cis-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]8b), trans-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]10a), trans-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]10b), cis-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]12a), and trans-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]13a), were designed and synthesized as potential PET probes for aryl hydrocarbon receptor (AhR) in cancers.

A simple access to biologically important trans-stilbenes via Ru-catalyzed cross metathesis

The cross metathesis of methoxy- or acetoxy-substituted styrenes using the Grubbs II catalyst affords unsymmetrical (mixed) E-stilbenes with astonishingly high selectivity (up to 79% yield). This approach offers a short and flexible synthesis of variously substituted stilbenes, which are derivatives or precursors of biologically important compounds such as resveratrol, piceatannol, and pinostilbene. Georg Thieme Verlag Stuttgart.

STILBENE DERIVATIVES AND THEIR USE IN MEDICAMENTS

The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R1 to R6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and s

Resveratrol analogues as selective cyclooxygenase-2 inhibitors: Synthesis and structure-activity relationship

A series of hydroxylated and methoxylated trans-stilbenes were synthesized and evaluated for their ability to inhibit COX-1 and COX-2. Some of the hydroxylated derivatives are highly selective COX-2 inhibitor with potency comparable or better than clinically established drugs. Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is found in grapes and various medical plants. Among cytotoxic, antifungal, antibacterial cardioprotective activity resveratrol also demonstrates non-selective cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibition. In order to find more selective COX-2 inhibitors a series of methoxylated and hydroxylated resveratrol derivatives were synthesized and evaluated for their ability to inhibit both enzymes using in vitro inhibition assays for COX-1 and COX-2 by measuring PGE2 production. Hydroxylated but not methoxylated resveratrol derivatives showed a high rate of inhibition. The most potent resveratrol compounds were 3,3′,4′,5-tetra-trans-hydroxystilbene (COX-1: IC50 = 4.713, COX-2: IC50 = 0.0113 μM, selectivity index = 417.08) and 3,3′,4,4′,5,5′-hexa-hydroxy-trans-stilbene (COX-1: IC 50 = 0.748, COX-2: IC50 = 0.00104 μM, selectivity index = 719.23). Their selectivity index was in part higher than celecoxib, a selective COX-2 inhibitor already established on the market (COX-1: IC 50 = 19.026, COX-2: IC50 = 0.03482 μM, selectivity index = 546.41). Effect of structural parameters on COX-2 inhibition was evaluated by quantitative structure-activity relationship (QSAR) analysis and a high correlation was found with the topological surface area TPSA (r = 0.93). Docking studies on both COX-1 and COX-2 protein structures also revealed that hydroxylated but not methoxylated resveratrol analogues are able to bind to the previously identified binding sites of the enzymes. Hydroxylated resveratrol analogues therefore represent a novel class of highly selective COX-2 inhibitors and promising candidates for in vivo studies.