190439-39-5

Usage

Structure

Benzene ring fused to an imidazole ring

Substituents

5-methoxy on the benzene ring, 4-nitrophenyl on the imidazole ring

Derivative

Benzimidazole

Applications

Pharmaceutical research (antimicrobial, anti-inflammatory, and anticancer properties)

Potential uses

Fluorescent probe, chemical synthesis

Additional research

Needed to explore potential uses and properties further

Upstream product

• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 96633-78-2 N-(4-methoxyphenyl)-4-nitrobenzylamine oxime 
• 1042161-74-9 C₁₄H₁₁N₅O₃ 
• 555-16-8 4-nitrobenzaldehdye 

Relevant academic research and scientific papers

A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity

Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a–3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a–4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H37RV, MIC at 16 μM and 24 μM respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.

Investigation of O-Sulfonylation-promoted Heterolytic N?O Bond Cleavage of Amidoximes and Ketoximes

Two different reaction pathways were observed in the sulfonylation of N-phenylbenzamidoximes. The reaction with o-NsCl at a heating temperature gave N,N′-diphenylureas via Tiemann rearrangement, while the reaction with Ts2O at a lower temperature formed 2-phenylbenzimidazoles via intramolecular electrophilic aromatic substitution. When the amide nitrogen was replaced with carbon substituents, oxime derivatives of benzoins and benzils underwent Beckmann fragmentation reactions upon sulfonylation, whereas sulfonylation of 2-phenylacetophenone oxime afforded exclusively the Beckmann rearrangement adduct.

A simple and straightforward synthesis of substituted 2-arylbenzimidazoles over silica gel

A solid phase strategy for the synthesis of substituted 2-arylbenzimidazoles over silica gel has been achieved starting from their corresponding o-phenylenediamines 1 and aromatic aldehydes 2. The reaction is very simple, convenient and straightforward, a

Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides

(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.

Synthesis and antimicrobial activity of 1-dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives

1-(Dialkylaminomethyl)-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives 1 have been synthesized by reacting 2-phenylbenzimidazole derivatives with formaldehyde and a secondary amine. The derivatives of 2-phenylbenzimidazole were obtained by reacting the bisulfide addition product of substituted benzaldehydes with 4-substituted-o-phenylenediamines. Their structures were confirmed by microanalysis, IB and NMB spectral analysis. Antimicrobial activity of the compounds was investigated by the microdilution susceptibility test in Mueller-Hinton Broth and Sabouraud Dextrose Broth was used for the determination of antibacterial and antifungal activities. Test organisms: Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as Gram-positive bacteria, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853 as Gram-negative bacteria, and Candida albicans, C. parapsilosis, C. stellatoidea as yeast-like fungi. Compounds 1a, 1b, 1c, 1e and 1i showed slight to moderate activity against all microorganisms. Compound 1g showed the highest activity. It was found more potent than streptomycin against Enterococcus faecalis and Pseudomonas aeruginosa.

Studies on analgesic and anti-inflammatory activities of 1- dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives

In this study the analgesic and anti-inflammatory activity of 1,2,5- trisubstituted benzimidazole derivatives have been examined. Analgesic activities of these compounds were investigated by using the modified Koster test. Among the compounds synthesized especially compound 1g (1- diethylaminomethyl)-2-(p-chlorophenyl)-5-nitro benzimidazole hydrochloride) has shown higher activity than acetylsalicylic acid (ASA) and indometacin. Compound 1e (1-(diethylaminomethyl)-2-(p-methoxyphenyl)-5-nitro benzimidazole hydrochloride, 1f (1-(diethylaminomethyl)-2-(p-tolyl)-5-nitro henzimidazole hydrochloride and 1i (1-(pipenridinomethyl)-2-(p-methoxyphenyl)-5-nitro benzimidazole hydrochloride) proved as potent as the standard ASA. Therefore the compounds 1e, 1f, 1g and 1i were screened for their anti-inflammatory activities using the carrageenan-induced hind paw edema test. Except 1g all compounds were almost inactive against this model of inflammation compared to indometacin.