213133-77-8

Usage

Chemical Properties

White crystals

InChI:InChI=1/C9H8BrFO/c1-2-9(12)6-3-7(10)5-8(11)4-6/h3-5H,2H2,1H3

Upstream product

• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 95-50-1 1,2-dichloro-benzene 
• 95-54-5 1,2-diamino-benzene 
• 615-43-0 2-iodophenylamine 
• 6831-55-6 2-(3,4-dichlorophenyl)acetyl chloride 
• 1004177-28-9 2-(3,4-dichlorophenyl)-N-(2-iodophenyl)acetamide 
• 5807-30-7 3,4-dichlorophenyl acetic acid 

Downstream Products

• 1602748-35-5 methyl 2-(2-(3,4-dichlorobenzyl)-1H-benzo[d]imidazol-1-yl)acetate 
• 1602747-50-1 2-(2-(3,4-dichlorobenzyl)-1H-benzo[d]imidazol-1-yl)-N-(5-isopropyl-2-methylphenyl)acetamide 
• 1602747-55-6 N-(3,5-di-tert-butylphenyl)-2-(2-(3,4-dichlorobenzyl)-1H-benzo[d]imidazol-1-yl)acetamide 
• 1047731-79-2 2-(2-(3,4-dichlorobenzyl)-1H-benzo[d]imidazol-1-yl)acetic acid 

Relevant academic research and scientific papers

Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles with arenes in the Br?nsted superacid TfOH resulted in the formation of the corresponding Friedel-Crafts reaction products, 2-diarylmethyl and 2-arylmethyl-substituted benzimidazoles, in yields up to 90%. The reaction intermediates, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means of NMR and DFT calculations and plausible reaction mechanisms are discussed.

Synthesis method of benzimidazole derivative

The invention discloses a synthesis method of a benzimidazole derivative. The method comprises the following steps: o-phenylenediamine or a derivative thereof and phenylacetic acid or a derivative ofthe phenylacetic acid are used as raw materials, a composite solid catalyst is adopted, and a high-boiling-point organic solvent is taken as a reaction solvent for carrying out a reaction at 100-130 DEG C for 4-8 hours; and distillation, dissolution, neutralization, decoloration and recrystallization are carried out to obtain a benzimidazole derivative product. The method has the advantages that operation is simple, the reaction time is greatly shortened, the product color is good, the yield is high, cost is low, pollution is low, environment friendliness is achieved, and the like, and has a very good industrial production application prospect.

Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease

In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from Aβ-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD.

Exploration of 2-benzylbenzimidazole scaffold as novel inhibitor of NF-κB

For finding the novel inhibitor of nuclear factor κB activity, a series of benzimidazole derivatives were rationally designed, synthesized and systematically studied for their in vitro activities against LPS induced NF-κB inhibition in RAW 264.7 cells using the SEAP assay based on the flexible chalcone JSH ((E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxy phenyl)prop-2-en-1-one) which was previously reported. Although most of the benzimidazole derivatives showed strong inhibitory activity in low micromolar potency, 2-(4-methoxybenzyl)-1H-benzo[d]imidazole (3m; IC50 = 1.7 μM) and 2-(2-methoxybenzyl)-1H-benzo[d]imidazole (3n; IC50 = 2.4 μM) showed the best inhibition. The structure activity relationship revealed that 2-benzylbenzimidazole scaffold with hydrogen bonding acceptor on phenyl ring appears as a pharmacophore.

BENZIMIDAZOLE DERIVATIVES AS MITOCHONDRIAL FUNCTION MODULATORS

Provided are a benzimidazole derivative modulating mitochondrial functions and having pharmaceutical activity as a neuro-protective agent, and a pharmaceutical composition including the compound as an active ingredient.