51597-75-2

Upstream product

• 73308-34-6 3-(3,4-Dichloro-phenyl)-2,5-diphenyl-thiazolidin-4-one 
• 100-52-7 benzaldehyde 
• 95-76-1 m,p-dichloroaniline 
• 100-51-6 benzyl alcohol 
• 99-54-7 3,4-dichloronitrobenzene 

Relevant academic research and scientific papers

Binding Mode Characterization and Early in Vivo Evaluation of Fragment-Like Thiols as Inhibitors of the Virulence Factor LasB from Pseudomonas aeruginosa

The increasing emergence of antibiotic resistance necessitates the development of anti-infectives with novel modes of action. Targeting bacterial virulence is considered a promising approach to develop novel antibiotics with reduced selection pressure. The extracellular collagenase elastase (LasB) plays a pivotal role in the infection process of Pseudomonas aeruginosa and therefore represents an attractive antivirulence target. Mercaptoacetamide-based thiols have been reported to inhibit LasB as well as collagenases from clostridia and bacillus species. The present work provides an insight into the structure-activity relationship (SAR) of these fragment-like LasB inhibitors, demonstrating an inverse activity profile compared to similar inhibitors of clostridial collagenase H (ColH). An X-ray cocrystal structure is presented, revealing distinct binding of two compounds to the active site of LasB, which unexpectedly maintains an open conformation. We further demonstrate in vivo efficacy in a Galleria mellonella infection model and high selectivity of the LasB inhibitors toward human matrix metalloproteinases (MMPs).

Magnetic nanoparticle-supported phosphine gold(i) complex: A highly efficient and recyclable catalyst for the direct reductive amination of aldehydes and ketones

The direct reductive amination of aldehydes and ketones has been achieved in dichloromethane at room temperature by using a magnetic nanoparticle-supported phosphine gold(i) complex [Fe3O4@SiO2-P-AuCl] as the catalyst and ethyl Hantzsch ester as the hydrogen source, yielding a variety of secondary amines in excellent yields under neutral conditions. The new heterogeneous gold catalyst can be prepared by a simple procedure from commercially readily available reagents and can easily be separated from the reaction mixture by applying an external magnet and recycled at least 10 times without any loss of activity.

Direct reductive amination of aldehydes with nitroarenes using bio-renewable formic acid as a hydrogen source

Reductive amination (RA) is one of the most important transformations in organic chemistry. A versatile and sustainable gas-free RA of aldehydes carried out directly with cheaply available nitroarenes using stoichiometric amounts of non-toxic and entirely renewable formic acid (FA) as the terminal reductant is described herein. A single phase rutile titania supported gold (Au/TiO2-R) catalyst is shown to catalyse efficiently this FA-based direct RA in neat water under mild reaction conditions. The broad scope, mild and neutral conditions, together with CO2 and water as environmental harmless byproducts, make this transformation very useful. Moreover, straightforward examples of the direct construction of bioactive heterocyclic compounds containing a benzimidazole motif were achieved through this protocol.

Pd@[nBu4][Br] as a simple catalytic system for N-alkylation reactions with alcohols

Palladium nanoparticles, simply and briefly generated in commercial and cheap onium salts using supercritical carbon dioxide, have been found to be an effective catalytic system for additive free N-alkylation reaction using alcohols via cascade oxidation/condensation/reduction steps.

Reinvestigating Raney nickel mediated selective alkylation of amines with alcohols via hydrogen autotransfer methodology

An efficient, cost-effective use of Raney nickel (R-Ni) a widely used industrial catalyst for N-alkylation using alcohols is highlighted here. The work describes the scope and capability of R-Ni in hydrogen autotransfer reactions enabling its widespread use in the Chemical and Pharmaceutical industry. R-Ni of W4, T4, and W7 grades were prepared and evaluated for alkylation of amines. The best activity and selectivity for mono alkylation of amines were obtained using W4 R-Ni at 1:4 moles of amine to alcohol in xylene at reflux. T4 R-Ni also showed ability to form stable imines. The prepared R-Ni was also recycled and reused for N-alkylation reaction. The optimized methodology was applied for synthesis of Active Pharmaceutical ingredients Piribedil and Mepyramine. The simplicity and wide substrate scope makes this method a preferred Hydrogen Auto-transfer protocol for the alkylation of amines.

N-Alkylation of amines with alcohols over nanosized zeolite beta

Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.

Single pot reductive animation of aromatic aldehydes to N-arylamines

Aromatic aldehydes are directly converted into N-arylamines in a single reaction sequence in the presence of sodium borohydride. The products are obtained in good yield and purity for direct utilization.

The NMR Spectra of the Porphyrins 17. Metalloporphyrins as Diamagnetic Shift Reagents, Structural and Specificity Studies

The nature of the metalloporphyrin-ligand complexes produced by zinc, magnesium and cobalt porphyrins with basic ligands has been investigated using the diamagnetic ring current shifts of the porphyrin on the ligand protons.The metal to nitrogen bond lengths in some metallo-meso-tetraphenylporphyrin (pyridine) complexes have been determined and compared with the data of the crystalline complexes.The geometry of the Zn meso-tetraphenylporphyrin complexes with 2-picoline, quinoline and isoquinoline has been investigated.Steric interactions between the ligand and the porphyrin in 2-picoline and quinoline produce a dramatic increase in the Zn-N bond length when compared to the unstrained analogues pyridine and isoquinoline.This large increase is associated with comparatively minor angle distortions in the complex.The specificity of the Zn meso-tetraphenylporphyrin complexation shifts has been determined for a range of benzyl and butyl compounds.The complexation shift is linearly related to the basicity of the ligand for a wide range of basicities.

Reductive Ring Contraction of Mesoionic Thiazol-4-ones to Azetidin-2-ones

A series of anhydro-2,3,5-triaryl-4-hydroxythiazolium hydroxides was prepared and desulfurized with Raney nickel.The reduction was stereospecific and gave cis-1,3,4-triphenylazetidin-2-ones.Desulfurization in the presence of triphenylphosphine gave the corresponding trans-azetidinones.Consideration of the possible mechanistic pathways led to the conclusion that the reaction proceeds through formation of biradical-dipole, hydrogenation to a 1,4-dipole, and ring closure.It was also concluded that in the preparation of β-lactams by the nonconcerted cycloaddition of imines and ketenes the first step (dipole formation) is the stereochemistry-determining step.

Method of topically treating inflammation

This invention describes a method of treating inflammation in warmblooded animals by topically administering an effective amount of benzylamine and its derivatives.