223377-41-1

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 1003-09-4 2-bromothiophene 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 2746-25-0 p-Methoxybenzyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 71722-33-3 2,2'-dithienyliodonium bromide 
• 768-60-5 4-methoxyphenylacetylen 
• 696-62-8 para-iodoanisole 
• 548474-55-1 Trimethyl-((E)-2-thiophen-2-yl-vinyl)-silane 

Downstream Products

• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Antiradical Properties of trans-2-(4-substituted-styryl)-thiophene

2-substituted thiophene compounds with electron donating and electron withdrawing p-phenyl substitution were synthesized and studied their radical scavenging properties using DPPH assay and DFT method. It is shown that p-hydroxy and p-amino phenyl substit

New uncharged 2-thienostilbene oximes as reactivators of organophosphate-inhibited cholinesterases

The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) by organophosphates (OPs) as nerve agents and pesticides compromises normal cholinergic nerve signal transduction in the peripheral and central nervous systems (CNS) leading to cholinergic crisis. The treatment comprises an antimuscarinic drug and an oxime reactivator of the inhibited enzyme. Oximes in use have quaternary nitrogens, and therefore poorly cross the brain–blood barrier. In this work, we synthesized novel uncharged thienostilbene oximes by the Wittig reaction, converted to aldehydes by Vilsmeier formylation, and transformed to the corresponding uncharged oximes in very high yields. Eight trans,anti-and trans,syn-isomers of oximes were tested as reactivators of nerve-agent-inhibited AChE and BChE. Four derivatives reactivated cyclosarin-inhibited BChE up to 70% in two hours of reactivation, and docking studies confirmed their productive interactions with the active site of cyclosarin-inhibited BChE. Based on the moderate binding affinity of both AChE and BChE for all selected oximes, and in silico evaluated ADME properties regarding lipophilicity and CNS activity, these compounds present a new class of oximes with the potential for further development of CNS-active therapeutics in OP poisoning.

Substituent Dependent Optical Properties of p-phenyl Substituted ethenyl-E-thiophenes

Various electron donor and acceptor substituted (NO2, CN, Cl, H, OCH3, NH2) p-phenyl ethenyl-E- thiophenes (1–6) were synthesized and substituent dependent optical properties (dipole moment, transition dipole moment, oscillator strength, optical band gap, hyperpolarizability) were studied using Solvatochromism and Density functional theory. It is shown that thiophene acts as a weak electron donor in presence of an electron withdrawing p-phenyl substituent (NO2, CN, Cl), whereas thiophene acts as a weak electron acceptor in presence of an electron donating p-phenyl substituent (OCH3, NH2). In comparison to ethenyl thiophene 4, the HOMO-LUMO energy band gap is decreased upon increasing the electron donating or electron withdrawing capacity of p-phenyl substituent. From the excited state dipole moment calculation, it is shown that the excited state is highly dipolar for nitro and amino compounds 1 and 6, whereas compounds 2–5 show a non-polar excited state. As compared to the ethenyl thiophene 4, the first hyperpolarizability (β) increases upon substitution either with a strong electron withdrawing or strong electron donating p-phenyl substituent. A large β value is found for p-nitro phenyl ethenyl-E-thiophene and p-amino phenyl ethenyl-E- thiophene. Overall, these studies provide useful information in understanding the optical properties of phenyl and heterocyclic based ethenyl systems.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

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.

Synthesis of areno[e]indenes by the flash vacuum pyrolysis of 4-methoxystyrylarenes

Flash vacuum pyrolysis of 4-methoxystyrylarenes (1b-e) at 800°C and ca. 1×10-2 Torr gave the corresponding areno[e]indenes (3b-e) as the major products and 4-hydroxystyrylarenes (4b-e) as the miner ones.

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.

The cross-coupling reaction of vinylindiums generated via hydroindation of terminal alkynes with diaryliodoniums salts

In InCl3-NaBH4-MeCN system, vinylindiums generated by hydroindation of aryl terminal alkynes can undergo cross-coupling reaction with diaryliodonium salts high regio- and stereoselectively. But under the same conditions, the aliphatic terminal alkynes do not react very well.

Styrylheterocycles: A novel class of inhibitors on lipopolysaccharide-Induced nitric oxide production

A series of styrylheterocycles was prepared and their inhibitory activities against nitric oxide (NO) production were evaluated in a cell culture system using lipopolysaccharide-stimulated RAW264.7 macrophage cells. Our studies have identified a new series of inhibitors on NO production, providing the basis for further development of potent inhibitors. The preliminary structure-activity relationship, to elucidate the essential structural requirements, has been described. Mechanistic studies suggest that the suppression of iNOS mRNA transcription is, at least in part, related to the inhibitory activity of styrylheterocycles.