77123-67-2

Usage

Structure

Contains a benzimidazole ring with a bromine atom replacing one of the hydrogen atoms in the benzene ring

Usage

Commonly used as a building block in organic synthesis and pharmaceutical research

Therapeutic potential

Known for its potential therapeutic applications, including anti-cancer, anti-viral, and anti-inflammatory effects

Research interest

Of interest to researchers in the fields of medicinal chemistry and drug development due to its unique structure and potential biological activity.

InChI:InChI=1/C13H10BrN3/c14-8-5-6-10(15)9(7-8)13-16-11-3-1-2-4-12(11)17-13/h1-7H,15H2,(H,16,17)

Upstream product

• 66416-72-6 4-bromo-2-iodoaniline 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 5805-39-0 2-(aminophenyl)benzimidazole 

Downstream Products

• 77123-54-7 10-bromo-6-(3-bromophenyl)benzimidazoquinazoline 
• 134662-89-8 [2-(1H-Benzoimidazol-2-yl)-4-bromo-phenyl]-[1-(2-nitro-phenyl)-meth-(E)-ylidene]-amine 
• 134662-76-3 2-Bromo-6-(2-nitro-phenyl)-5,6-dihydro-benzo[4,5]imidazo[1,2-c]quinazoline 
• 134662-82-1 2-Bromo-6-(2-nitro-phenyl)-benzo[4,5]imidazo[1,2-c]quinazoline 
• 77123-68-3 10-<(trimethylsilyl)ethynyl>-6-<3-<(trimethylsilyl)ethynyl>phenyl>benzimidazoquinazoline 
• 77123-69-4 10-ethynyl-6-(3-ethynylphenyl)benzimidazoquinazoline 

Relevant academic research and scientific papers

Benzimidazoquinazolines as new potent anti-TB chemotypes: Design, synthesis, and biological evaluation

In search for new molecular entities as anti-TB agents, the benzimidazoquinazoline polyheterocyclic scaffold has been designed adopting the scaffold hopping strategy. Thirty-two compounds have been synthesized through an improved tandem decarboxylative nucleophilic addition cyclocondensation reaction of o-phenylenediamine with isatoic anhydride followed by further cyclocondensation of the intermediately formed 2-(o-aminoaryl)benzimidazole with trialkyl orthoformate/acetate. The resultant benzimidazoquinazolines were evaluated in vitro for anti-TB activity against M. tuberculosis H37Rv (ATCC27294 strain). Fourteen compounds exhibiting MIC values in the range of 0.4–6.25 μg/mL were subjected to cell viability test against RAW 264.7 cell lines and were found to be non-toxic (30% inhibition at 50 μg/mL). The active compounds were further evaluated against INH resistant Mtb strains. The most active compound 6x [MIC (H37Rv) of 0.4 μg/mL] and the compound 6d [MIC (H37Rv) of 0.78 μg/mL] were also found to be active against INH resistant Mtb strain with MIC values of 12.5 and 0.78 μg/mL, respectively.

Palladium-Catalyzed Cyclization Reaction of o-Iodoanilines, CO2, and CO: Access to Isatoic Anhydrides

Isatoic anhydrides, a class of valuable synthetic intermediates and RNA structure probing reagents, are usually prepared with highly toxic phosgene or stoichiometric oxidants. Herein we report a highly selective palladium-catalyzed cyclization reaction for the efficient synthesis of isatoic anhydrides from readily available o-iodoanilines, CO2, and CO. The reaction proceeds under mild conditions and is redox-neutral. Both CO2 and CO are indispensable C1 building blocks for this catalytic reaction.

Facile Synthesis of Ethynylated Benzoic Acid Derivatives and Aromatic Compounds via Ethynyltrimethylsilane

The coupling reaction between an aromatic halide and ethynyltrimethylsilane under the catalysis of palladium(0) generated in situ, followed by treatment of the (trimethylsilyl)ethynyl product with potassium carbonate in methanol at ambient temperatures, provides a simple approach to various ethynylated benzoic acid derivatives and other aromatic compounds.The conditions for the removal of the trimethylsilyl group were very mild, so that base-sensitive functionalities on the aromatic moiety could be tolerated.