7431-35-8

Upstream product

• 140-29-4 phenylacetonitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 72433-39-7 (Z)-α-Phenyl-β-nitro-4-nitrocinnamonitril 
• 52565-63-6 (Z)-3-(4-aminophenyl)-2-phenylacrylonitrile 
• 112934-24-4 2-phenyl-3-(p-aminophenyl)acrylonitrile 
• 3769-84-4 p-nitrodeoxybenzoin 

Relevant academic research and scientific papers

Highly active g-C3N4 as a solid base catalyst for knoevenagel condensation reaction under phase transfer conditions

In a promising approach, heterogeneous g-C3N4 as a solid base catalyst exhibits appreciable activity in Knoevenagel condensations at room temperature for the synthesis of substituted stilbene in presence of a crown-ether phase transfer catalyst. High yield of the product substituted stilbene were isolated in a very short reaction time period (～30 min). The solid base g-C3N4 catalyst was proven to be recyclable for several runs. Various aromatic substrates were screened using heterogeneous base g-C3N4 catalyst, exhibiting appreciable corresponding product yield (～99%) at room temperature.

A Catalytic Peterson-like Synthesis of Alkenyl Nitriles

A heterogeneous fluoride catalyst was found to enable the straightforward formation of alkenyl nitriles from the reaction of aldehydes and simple or substituted acetonitriles, in the presence of commercially available silazanes and in solvent-free conditions. The protocol afforded the products in good to excellent yields with selectivity values dependent on the nature of the substrates. It represents an alternative to classic approaches using stoichiometric strong bases, and the catalyst can be easily recovered and reused for consecutive cycles.

Thermal rearrangement of 2,3-diaryl-1-phthalimidoaziridines

2,3-Diaryl-1-phthalimidoaziridines and 2,3-diaryl-1-phthalimidoaziridine-2-carbonitriles were found to readily undergo thermal rearrangement into imines via 1,2-migration of the phthalimido group and accompanying C-C bond cleavage. Isomerization proceeds regioselectively with preferable migration to the electron-deficient carbon atom. Interestingly, this reaction was found to predominate even in the presence of dipolarophiles.

Quantitative and highly selective sensing of sodium houttuyfonate via long-aliphatic chains hydrophobic assembly and aggregation-induced emission

A new α-cyanostilbene derivative, CDB-DMA12, was designed and synthesized as a supramolecular chemosensor for the detection of sodium houttuyfonate (SH) via aggregation-induced emission enhancement (AIEE), which could efficiently bind with SH, then induce an obvious fluorescence enhancement and visible absorption red-shifting (by the naked eye). Accordingly, a linear relationship was found when plotting the fluorescence intensity at 558 nm against SH concentration, with an estimated detection limit of 8.5 μM. Interestingly, morphology changes from nanoparticles to sheet, scroll and tube-shaped aggregates were observed on CDB-DMA12 after the addition of SH. Moreover, CDB-DMA12 showed high selectivity to SH among other sulfonyl containing species, which is attributed to the synergistic effect of its quaternary ammonium, the hydrogen bonding of the active group sites and the twelve carbon containing long-aliphatic chain units. In addition, the results paved a new way for the detection/recognition of amphiphilic natural products in aqueous solution with high sensitivity and selectivity. Besides, it provided a possible approach for the preparation of new fluorescent micro/nano-scaled architectures through the solution self-assembly of oppositely-charged amphiphiles.

NAPHTHALENE DERIVATIVE

The present invention provides compounds which can regulate VCP activity. The present invention provides the compound of formula (I) (R is as defined in the description) or oxides, esters, prodrugs, pharmaceutically acceptable salts or solvates thereof. The compounds can regulate VCP activity, and thus are useful for treating VCP-mediated diseases such as neurodegenerative diseases.

Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents

In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or p-nitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure-activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains.

(Z)-2-(2-bromophenyl)-3-{[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172): An orally bioavailable PPARβ/δ-selective ligand with inverse agonistic properties

The ligand-regulated nuclear receptor peroxisome proliferator-activated receptor β/δ (PPARβ/δ) is a potential pharmacological target due to its role in disease-related biological processes. We used TR-FRET-based competitive ligand binding and coregulator

Monoalkylations with alcohols by a cascade reaction on bifunctional solid catalysts: Reaction kinetics and mechanism

A bifunctional catalytic system formed by Pd on MgO catalyzes the cascade process between benzyl alcohol and phenylacetonitrile, diethylmalonate and nitromethane, to give the respective α-monoalkylated products without external supply of hydrogen. The process involves a series of three cascade reactions occurring on different catalytic sites. The alcohol undergoes oxidation to the corresponding aldehyde with the simultaneous formation of a metal hydride; then, the aldehyde reacts with a nucleophile formed "in situ" to give an alkene, and finally, the hydrogen from the hydride is transferred to the alkene to give a new C-C bond. A kinetic study on the α-monoalkylation reaction of benzylacetonitrile with benzyl alcohol reveals that the rate-controlling step for the one-pot reaction sequence is the hydrogen transfer reaction from the surface hydrides to the olefin, and consequently, the global reaction rate is improved when decreasing the size of the Pd metal particle.

Chiral recognition based on enantioselectively aggregation-induced emission

(Figure Presented) Novel chiral AIE compounds bearing a tartaric acid group were synthesized. They selectively aggregated with one enantiomer of a number of chiral amines, such that one enantiomer led to strong fluorescence and another enantiomer showed no or only weak fluorescence. This was used for the quantitative analysis of enantiomeric composition.

Environmentally friendly one-pot synthesis of α-alkylated nitriles using hydrotalcite-supported metal species as multifunctional solid catalysts

A ruthenium-grafted hydrotalcite (Ru/HT) and hydrotalcite-supported palladium nanoparticles (Pdnano/ HT) are easily prepared by treating basic layered double hydroxide, hydrotalcite (HT, Mg6Al 2(OH)16CO3) with aqueous RuCl 3·n H2O and K2[PdCl4] solutions, respectively, using surface impregnation methods. Analysis by means of X-ray diffraction, and energydispersive X-ray, electron paramagnetic resonance, and X-ray absorption fine structure spectroscopies proves that a monomeric RuIV species is grafted onto the surface of the HT. Meanwhile, after reduction of a surface-isolated PdII species, highly dispersed Pd nanoclusters with a mean diameter of about 70 A is observed on the Pdnano/HT surface by transmission electron microscopy analysis. These hydrotalcite-supported metal catalysts can effectively promote α-alkylation reactions of various nitriles with primary alcohols or carbonyl compounds through tandem reactions consisting of metal-catalyzed oxidation and reduction, and an aldol reaction promoted by the base sites of the HT. In these catalytic α-alkylations, homogeneous bases are unnecessary and the only by-product is water. Additionally, these catalyst systems are applicable to one-pot syntheses of glutaronitrile derivatives.