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Relevant academic research and scientific papers

Design, synthesis, and computational studies of benzimidazole derivatives as new antitubercular agents

The increase in the drug-resistant strains of Mycobacterium tuberculosis has led researchers to new drug targets. The development of new compounds that have effective inhibitory properties with the selective vital structure of Mycobacterium tuberculosis is required in new scientific approaches. The most important of these approaches is the development of inhibitor molecules for Mycobacterium cell wall targets. In this study, first of all, the antitubercular activity of 23 benzimidazole derivatives was experimentally determined. And then molecular docking studies were carried out with 4 different targets: Arabinosyltransferase C (EmbC), Filamentous Temperature Sensitive Mutant Z (FtsZ), Protein Tyrosine Phosphatase B (PtpB), and Decaprenylphosphoryl-β-D-ribose-2′-oxidase (DprE1). It has been determined that benzimidazole derivatives show activity through the DprE1 enzyme. It is known that DprE1, which has an important role in the synthesis of the cell envelope from Arabinogalactan, is also effective in the formation of drug resistance. Due to this feature, the DprE1 enzyme has become an important target for drug development studies. Also, it was chosen as a target for this study. This study aims to identify molecules that inhibit DprE1 for the development of more potent and selective antitubercular drugs. For this purpose, molecular docking studies by AutoDock Vina, and CDOCKER and molecular dynamics (MD) simulations and in silico ADME/Tox analysis were implemented for 23 molecules. The molecules exhibited binding affinity values of less than ?8.0 kcal/mol. After determining the compound’s anti-TB activities by a screening test, the best-docked results were detected using compounds 20, 21, and 30. It was found that 21, was the best molecule with its binding affinity value, which was supported by MD simulations and in silico ADME modeling results. Communicated by Ramaswamy H. Sarma.

Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound3bcan be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 × 104M?M, respectively.

Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for selective synthesis of benzimidazoles

Polystyrene-supported pyridinium chloroaluminate ionic liquid was prepared from the reaction of a Merrifield resin with pyridine followed by reaction with aluminium chloride. This catalyst was used as a new chemoselective Lewis acid catalyst for the exclusive synthesis of 2-substituted benzimidazoles from the reaction of aldehydes with o-phenylenediamines. The catalyst was stable (as a benchtop catalyst) and could easily be recovered and reused without appreciable change in its efficiency.

A general approach to substituted benzimidazoles and benzoxazoles via heterogeneous palladium-catalyzed hydrogen-transfer with primary amines

The synthesis of benzimidazoles starting from o-phenylenediamines and amines in the presence of palladium on charcoal as catalyst is reported. Under microwave dielectric heating it is possible to use a tertiary, a secondary, and even a primary amine as the substrate for a palladium-mediated process to get 2-substituted or 1,2-disubstituted benzimidazoles, depending on the nature of the o-phenylenediamine employed. Primary amines are the most suitable reagents for the atom economy of the overall process that resulted to be general as several different substituted benzimidazoles were obtained in good yield. Benzoxazoles can be also prepared starting from primary amines and o-aminophenol. The reaction is also highly selective as no (poly)-alkylated phenylenediamines or cross-contaminated benzimidazoles are obtained starting from N-monoalkylphenylenediamines. This behavior was interpreted as a scarce aptitude to dehydrogenation of the methylene bonded to the aromatic NH of N-alkylarylamines. The experiments carried out consent to draw an almost complete picture of the reaction pathways occurring during the process. The catalyst can be recycled several times and, although far from optimal performances, catalyst TON=90 is encouraging for further large-scale optimization protocols. In addition, the palladium on charcoal-catalyzed microwave-assisted reaction of o-phenylenediamine gives de-alkylation of tertiary amines and transformation into the secondary ones. Copyright

A general approach to substituted benzimidazoles and benzoxazoles via heterogeneous palladium-catalyzed hydrogen-transfer with primary amines

The synthesis of benzimidazoles starting from o-phenylenediamines and amines in the presence of palladium on charcoal as catalyst is reported. Under microwave dielectric heating it is possible to use a tertiary, a secondary, and even a primary amine as the substrate for a palladium-mediated process to get 2-substituted or 1,2-disubstituted benzimidazoles, depending on the nature of the o-phenylenediamine employed. Primary amines are the most suitable reagents for the atom economy of the overall process that resulted to be general as several different substituted benzimidazoles were obtained in good yield. Benzoxazoles can be also prepared starting from primary amines and o-aminophenol. The reaction is also highly selective as no (poly)-alkylated phenylenediamines or cross-contaminated benzimidazoles are obtained starting from N-monoalkylphenylenediamines. This behavior was interpreted as a scarce aptitude to dehydrogenation of the methylene bonded to the aromatic NH of N-alkylarylamines. The experiments carried out consent to draw an almost complete picture of the reaction pathways occurring during the process. The catalyst can be recycled several times and, although far from optimal performances, catalyst TON=90 is encouraging for further large-scale optimization protocols. In addition, the palladium on charcoal-catalyzed microwave-assisted reaction of o-phenylenediamine gives de-alkylation of tertiary amines and transformation into the secondary ones. Copyright

N-chlorosuccinimide/sodium hydroxide-mediated synthesis of benzimidazoles from amidines under mild conditions

A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.

Synthesis of 2-alkyl-substituted benzimidazoles by thermal decomposition of 2-azidobenzenamines in the presence of an aldehyde

2-Substituted benzimidazoles were prepared by reaction of 2-azidoaminobenzenes with aldehydes under thermal conditions. The reaction probably proceeds via a sequential imine formation, azide decomposition forming a nitrene, and electrocyclization. Copyright Taylor & Francis Group, LLC.

Synthesis and microbiological activity of 5(or 6)-methyl-2-substituted benzoxazole and benzimidazole derivatives

The synthesis and microbiological activity of a new series of 5(or 6)- methyl-2-substituted benzoxazoles (IVa-n) and benzimidazoles (Va-h) were described. The in vitro microbiological activity of the compounds was determined against gram-positive, gram-ne

Syntheses of condensed imidazoles by lead tetraacetate oxidation of amidines

2-Phenylbenzimidazoles, 2-benzylbenzimidazoles, 2-phenyl-1H-naphtholimidazole, and 2-benzyl-1H-naphtholimidazole have been synthesized in excellent yields (77-98percent) by lead tetraacetate oxidation of suitable N-arylbenzimides, N-arylphenylacetamidines, N-α-naphthylbenzimidine, and N-α-naphthylphenylacetamidine respectively.The mechanism of nitrene insertation and intramolecular competitive nitrene insertation leading to these heterocycles has also been discussed.