42970-79-6

Upstream product

• 1124-65-8 3-(2-thienyl)-2-propenoic acid 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 127-09-3 sodium acetate 
• 67-64-1 acetone 
• 15690-25-2 3-(2-thienyl)acrylic acid 
• 98-03-3 thiophene-2-carbaldehyde 
• 100-14-1 4-nitrobenzyl chloride 
• 2767-70-6 (p-nitrobenzyl)triphenylphosphonium bromide 
• 1918-82-7 2-vinylthiophene 
• 586-78-7 para-nitrophenyl bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 104-03-0 4-nitrobenzeneacetic acid 
• 39980-20-6 dimethyl (4-nitrobenzyl)phosphonate 

Downstream Products

• 41839-01-4 4-(2ξ-[2]thienyl-vinyl)-aniline 
• 67248-95-7 5-[2-(p-nitrophenyl)vinyl]-2-thiophenecarbaldehyde 
• 41839-01-4 (E)-4-(2-(thiophen-2-yl)vinyl)aniline 
• 177087-86-4 2-[(E)-(5-formyl)-2-thienylvinyl]-5-((E)-4-nitrostyryl)thiophene 

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.

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.).

Determining the excited-state substituent constants of furyl and thienyl groups

Six series of styrene derivatives XCH═CHArY (total of 65) containing the styrene parent molecular skeleton were synthesized (here, Y is OMe, Me, H, F, Cl, CF3, CN, and NO2, and X is 2-furyl, 3-furyl, 2′-methyl-2-furyl, 2-thienyl, 3-thienyl, and 2′-methyl-2-theniyl). Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelength of absorption maximum λmax was recorded. For the wavenumber νmax (cm?1, νmax?=?1/λmax) of the obtained λmax, a quantitative correlation analysis was performed, and 6 excited-state substituent constants σexcc(p) of groups X were obtained by means of curve-fitting method. Taking the νmax values of total 90 compounds of styrene derivatives as a data set (including 25 compounds from reference and 65 compounds of this work), a quantitative correlation analysis was performed, and the reliability of the obtained σexcc(p) was verified. In addition, 12 samples of disubstituted Schiff bases (XCH═NArY) involving the above groups X were synthesized, and their νmax values were recorded. Using these 12 νmax together with the 14 νmax values of Schiff bases taken from reference (total of 26 compounds), it was further verified that the σexcc(p) values are reliable by means of quantitative correlation method.

Substituent Dependence Charge Transfer and Photochemical Properties of Donor-Acceptor Substituted Ethenyl Thiophenes

Donor-acceptor conjugated molecules with efficient light induced properties represent interesting material for electronic device application. In this context, we have calculated excited state dipole moment of three ethenyl thiophenes (1–3) bearing varied

Synthesis and anticancer activity of new azo compounds containing extended π-conjugated systems

A series of novel azo compounds with extended π-conjugated systems were prepared by azo coupling reaction compounds trans-2-(4′-aminostyryl)-thiophene, 1-(4-aminophenyl)-4-phenyl-1,3-butadiene and 4-amino-4′-methoxystilbene with some phenols. The compounds were evaluated for their cytotoxicity against breast cancer adenocarcinoma (MCF-7), cervix adenocarcinoma (HeLa) and human embryonic kidney (HEK 293) cell lines using the MTT assay. The results showed all derivatives had more toxic effects than tamoxifen. Of all the compounds tested, the azo product obtained from coupling trans-2-(4′-Aminostyryl)-thiophene with 2-naphthol (compound 5b) exhibited the potent in vitro antiproliferative activity with IC50 27 ± 1 and 18 ± 0 μg/mL against MCF-7 and HeLa cell lines, respectively, while it was devoid of any cytotoxicity against normal HEK 293 cells even at 200 μg/mL.

Syntheses of NLO diamino chromophores containing imidazole and thiophene rings as conjugation linkage

Three nonlinear optical chromophores bearing diamino groups have been synthesised, in which imidazole and thiophene rings were employed as elongated conjugation bridges.

Regioselective photoamination of 2-styrylthiophenes with ammonia

Photoinduced electron transfer from the singlet excited state of 2-styrylthiophenes (1a-1f) to p-DCB (p-dicyanobenzene) has been proposed from the negative value of ΔGET (the free energy of the electron transfer) calculated by the Rehm-Weller e