3391-76-2

Upstream product

• 951163-68-1 methyl α-phenyl-4-hydroxy-3,4'-dimethoxycinnamic ester 
• 104-01-8 4-Methoxyphenylacetic acid 
• 121-33-5 vanillin 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 141-82-2 malonic acid 
• 696-62-8 para-iodoanisole 
• 637-69-4 4-Methoxystyrene 
• 97-54-1 2-methoxy-4-propenylphenol 
• 104-46-1 anethole 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 5932-68-3 (E)-2-methoxy-4-(1-propenyl)phenol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 7786-61-0 3-methoxy-4-hydroxystyrene 

Downstream Products

• 1192280-89-9 2-(4-hydroxy-3-methoxyphenyl)-2-(4'-methoxyphenyl)acetaldehyde 
• 93899-23-1 4-hydroxy-3,4'-dimethoxy-benzophenone 

Relevant academic research and scientific papers

Stilbene synthesis through decarboxylative cross-coupling of substituted cinnamic acids with aryl halides

The Pd-catalyzed decarboxylative cross-coupling reaction between cinnamic acid and aryl iodide derivatives was studied using both homogeneous and heterogeneous Pd-catalysts. It was demonstrated that simple Pd(OAc)2 can catalyze this reaction wi

Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes

Nrf2, which is a member of the cap'n’ collar family of transcription factors, is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. The importance of inflammation and oxidative stress in many chronic diseases supports the concept that activation of anti-oxidant Nrf2 signaling may have therapeutic potential. A number of Nrf2 activators have entered into clinical trials. Nrf2 exists in the cytosol in complex with its binding partner Keap1, which is a thiol-rich redox-sensing protein. In response to oxidative and electrophilic stress, select cysteine residues of Keap1 are modified, which locks Keap1 in the Nrf2-Keap1 complex and allows newly synthesized Nrf2 to enter the nucleus. Numerous Nrf2-activating chemicals, including a number of natural products, are electrophiles that modify Keap1, often by Michael addition, leading to activation of Nrf2. One concern with the design of Nrf2 activators that are electrophilic covalent modifiers of Keap1 is the issue of selectivity. In the present study, substituted trans stilbenes were identified as activators of Nrf2. These activators of Nrf2 are not highly electrophilic and therefore are unlikely to activate Nrf2 through covalent modification of Keap1. Dose-response studies demonstrated that a range of substituents on either ring of the trans stilbenes, especially fluorine and methoxy substituents, influenced not only the sensitivity to activation, reflected in EC50values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2. The stilbene backbone appears to be a privileged scaffold for development of a new class of Nrf2 activators.

Hydroxylated di- and tri-styrylbenzenes, a new class of antiplasmodial agents: Discovery and mechanism of action

The first systematic evaluation of the antiplasmodial activity of the hydroxystilbene family of natural products and di/tristyrylbenzenes is described. A library of 27 diversely substituted hydroxy stilbenoids was rapidly synthesized using modified Knoevenagel-Perkin-decarboxylation-Heck sequences from readily available starting materials (i.e. hydroxybenzaldehyde-phenylacetic acid-arylhalide). These compounds were evaluated for in vitro antiplasmodial activity against three different strains of Plasmodium falciparum. Notably, 4,4′4′′-((1E,1′E,1′′E)-benzene-1,3,5-triyltris(ethene-2,1-diyl))tris(2,6-dimethoxyphenol) (27), an octupolar stilbenoid, showed IC50 (μM) values of 0.6, 0.5 and 1.36 while a distyrylbenzene (11) showed IC50 values of 0.9, 2.0 and 2.7 against 3D7 (chloroquine sensitive), Dd2 and Indo (chloroquine resistant) strains of Plasmodium falciparum respectively. Moreover, 27 and 11, which exhibited selectivity indices of 40 and >111 were also found to be nontoxic to the HeLa cell line. Microscopic studies revealed that the rings and trophozoites obtained from the 27 and 11 (an octupolar tristyrylbenzene and distyrylbenzene respectively) treated cultures were growth inhibited and morphologically deformed. These cultures also showed DNA fragmentation and loss of mitochondrial membrane potential (ΔΨm), suggestive of apoptotic death of the parasite. Together, these studies introduce di/tristyrylbenzenes as a new class of antimalarial agents.

POLYHYDROXYLATED (1-PHENYL-2-PHENYL) ETHYLENE DERIVATIVES AS AN ANTI-AGEING AND PHOTOPROTECTIVE AGENT

The present invention is directed towards the cosmetic use of at least one compound of formula (I) and/or solvates thereof and/or stereoisomers thereof: formula (I) in which groups A and B are different and: - A—* represents a disubstituted phenyl radical: formula (I′) - B—** represents a mono- or disubstituted phenyl radical: formula (I′′) or of a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I), for treating and/or preventing the signs of ageing and/or of photoageing of keratin materials, preferably of the skin.

Flash-metathesis for the coupling of sustainable (poly)hydroxyl β-methylstyrenes from essential oils

A cross-metathesis procedure was developed to synthetize symmetrical and non symmetrical stilbenes from sustainable resources. The reaction proceeds under solvent-free conditions and at low catalyst loading (down to 0.01 mol%) within a couple of minutes only (TOF up to 6.9 s-1), on multi-gram scale. The highly reactive β-methylstyrene substrates were homo-coupled not only as pure synthons but also as components of essential oils that were reacted directly in order to eliminate prior substrate isolation from the overall process.

ONE POT MULTICOMPONENT SYNTHESIS OF SOME NOVEL HYDROXY STILBENE DERIVATIVES WITH ALPHA, BETA-CARBONYL CONJUGATION UNDER MICROWAVE IRRADIATION

The present invention provides a method for the preparation of some novel multiconjugated 2- or 4-hydroxy substituted stilbenes. The method provides one pot multicomponent approach wherein 3-4 step reaction sequences viz. condensation, decarboxylation and Heck coupling occur simultaneously which results in an enhanced yield of desired products and reduced reaction times

Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols

Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.

Direct olefination of benzaldehydes into hydroxy functionalized oligo (p-phenylenevinylene)s via Pd-catalyzed heterodomino Knoevenagel- decarboxylation-Heck sequence and its application for fluoride sensing π-conjugated units

A new approach for one step olefination of benzaldehydes into hydroxy functionalized OPVs is achieved through the first domino Knoevenagel- decarboxylation-Heck sequence using a single catalyst system. The methodology also led to new oxygen based OPV scaffolds capable of selective and visible fluoride recognition in organic or aqueous medium.

Synthesis of substituted stilbenes via direct decarboxylative coupling of cinnamic acids with arylboronic acids-under palladium catalysis

Readily available cinnamic acids possessing a hydroxy group including ferulic acid efficiently undergo direct decarboxylative arylation under palladium catalysis to form hydroxylated stilbenes. The reaction of related acids is also described.

An efficient microwave-promoted route to (Z)-stilbenes from trans-cinnamic acids: Synthesis of combretastatin A-4 and analogues

cis-Stilbenes were synthesized from trans-cinnamic acids, involving ethylenic-bond bromination and a subsequent one-pot microwave-promoted stereoselective debrominative decarboxylation-Suzuki cross-coupling strategy. This sequence represents a useful way to prepare a variety of combretastatin A-4 derivatives.