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• 99-61-6 3-nitro-benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 83985-52-8 Cyclohexyl-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amine 

Relevant academic research and scientific papers

High-Throughput Screening of Reductive Amination Reactions Using Desorption Electrospray Ionization Mass Spectrometry

This study describes the latest generation of a high-throughput screening system that is capable of screening thousands of organic reactions in a single day. This system combines a liquid handling robot with desorption electrospray ionization (DESI) mass spectrometry (MS) for a rapid reaction mixture preparation, accelerated synthesis, and automated MS analysis. A total of 3840 unique reductive amination reactions were screened to demonstrate the throughputs that are capable with the system. Products, byproducts, and intermediates were all monitored in full-scan mass spectra, generating a complete view of the reaction progress. Tandem mass spectrometry experiments were conducted to verify the identity of the products formed. The amine and electrophile reactivity trends represented in the data match what is expected from theory, indicating that the system accurately models the reaction performance. The DESI results correlated well with those generated using more traditional mass spectrometry techniques like liquid chromatography-mass spectrometry, validating the data generated by the system.

Development of hydroxamate-based histone deacetylase inhibitors of bis-substituted aromatic amides with antitumor activities

Previously, we designed and synthesized a series of bis-substituted aromatic amide-based histone deacetylase (HDAC) inhibitors. In this study, we report the replacement of a bromine atom by different amides on the phenyl ring of the CAP region. Representa

Synthesis and evaluation of N-analogs of 1,2-diarylethane as Helicobacter pylori urease inhibitors

Therapies based on urease inhibition are now seriously considered as the first line of treatment for infections caused by Helicobacter pylori. However, the present inhibitors are ineffective or unstable in highly acidic gastric juice. Here, we report a series of benzylanilines as effective inhibitors of H. pylori urease. Out of the obtained twenty-one compounds, N-(3,4-dihydroxybenzyl)-4-nitroaniline (4) was evaluated in detail and shows promising features for development as anti-H. pylori agent. Excellent potency against urease in both cell-free extract and intact cell was observed at low concentrations of 4 (IC50 = 0.62 ± 0.04 and 1.92 ± 0.09 μM), which showed over 29- and 54-fold increase in potency with respect to the positive control AHA. The SAR analysis revealed that protection of 3,4-dihydroxy group of 4 as methoxy or changes of 4-NO2 will result in a moderate to dramatic decrease in potency.

Zinc phthalocyanine with PEG-400 as a recyclable catalytic system for selective reduction of aromatic nitro compounds

Zinc phthalocyanine with PEG-400 was established as a catalytic system for chemo and regioselective reduction of aromatic nitro compounds to corresponding amines. A large range of reducible functional groups such as acid, amide, ester, halogen, lactone, nitrile, N-benzyl, O-benzyl, hydroxy and heterocycles were well tolerated. Direct synthesis of benzotriazole from O-dinitrobenzene was achieved for the first time. The present catalytic system was successfully employed for the reduction of carbonyl and ester compounds to corresponding alcohols and reductive amination of benzaldehydes with primary amines to form corresponding secondary amines. Remarkable advantages of the present catalytic method include low loading of metal, avoidance of toxic ligands and high isolated yields. The catalyst was recyclable up to four times without any loss of selectivity and activity.

Ionic liquid-supported aldehyde: A highly efficient scavenger for primary amines

Novel aldehyde-functionalized ionic liquids have been synthesized and used as scavengers for primary amines in the synthesis of secondary amines. The yields of secondary amines are high (82-90%) with high purity. The advantages of the protocol over that w

S-Benzyl isothiouronium chloride as a recoverable organocatalyst for the direct reductive amination of aldehydes

The direct reductive amination of aldehydes using S-benzyl isothiouronium chloride as a recoverable organocatalyst for the activation of the imine intermediate through hydrogen bonding is described. A mild and operationally simple fragment coupling procedure was accomplished with a wide range of aldehydes as well as amines in good to excellent yields. In addition, the S-benzyl isothiouronium chloride catalyst was easily recovered by simple filtration and reused without any drop in its efficiency.

Coenzyme Model Studies. Part 3. Transimination and Reduction using NADH Models

N-Arylidenealkylamines (1) undergo transimination with aniline derivatives in glacial acetic acid.In the presence of 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine (Hantzsch ester) transimination is followed by reduction of the transimination products (3) but not of (1).Transimination also takes place in acetonitrile on treatment of the amines (1) with anilinium trifluoroacetate.These phenomena are analogous to transiminations at the catalytic sites of pyridoxal-dependent enzymes and a similar transimination is followed by reduction in the mechanism of glutamate dehydrogenase.

NADH Model Studies on the Glutamate Dehydrogenase Mechanism

N-Arylidenecyclohexylamines and anilines in glacial acetic acid are reduced by the Hantzch ester (3) to give the N-benzylaniline derivatives (6) in good yields by a route analogous to a suggested mechanism for glutamate dehydrogenase.