20076-54-4

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dichlorobenzimidazole is used as a chemical intermediate for the production of antifungal drugs, contributing to the development of medications that combat fungal infections.
Used in Oil and Gas Industry:
In the oil and gas sector, 5,6-Dichlorobenzimidazole is utilized as a potential corrosion inhibitor. Its application is aimed at preventing the growth of sulfate-reducing bacteria, which can cause corrosion in pipelines and other equipment.
Used in Chemical Synthesis:
5,6-Dichlorobenzimidazole is employed as a precursor in the synthesis of fluorescent dyes and pigments, playing a crucial role in the creation of materials with specific optical properties for various applications.
Given its importance across different industries, 5,6-Dichlorobenzimidazole is subject to regulatory controls to ensure its safe handling and use, reflecting the need for responsible management of its production and application.

Upstream product

• 19462-98-7 5,6-dichloro-2,3-dihydro-1H-1,3-benzodiazole-2-thione 
• 74-88-4 methyl iodide 
• 19462-98-7 5,6-dichloro-1H-benzimidazole-2-thiol 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 

Relevant academic research and scientific papers

Design, synthesis, and antitumor activity of PLGA nanoparticles incorporating a discovered benzimidazole derivative as EZH2 inhibitor

Purpose: Targeting enhancer of zeste homolog 2 (EZH2) can represent a hopeful strategy for oncotherapy. Also, the use of PLGA-based nanoparticles as a novel and rate-controlling carrier system was of our concern. Methods: Benzimidazole derivatives were synthesized, and their structures were clarified. In vitro antitumor activity was evaluated. Then, a modeling study was performed to investigate the ability of the most active compounds to recognize EZH2 active sites. Compound 30 (Drug) was selected to conduct pre-formulation studies and then it was incorporated into polymeric PLGA nanoparticles (NPs). NPs were then fully characterized to select an optimized formula (NP4) that subjected to further evaluation regarding antitumor activity and protein expression levels of EZH2 and EpCAM. Results: The results showed the antitumor activity of some synthesized derivatives. Docking outcomes demonstrated that Compound 30 was able to identify EZH2 active sites. NP4 exhibited promising findings and proved to keep the antitumor activity of Compound 30. HEPG-2 was the most sensitive for both Drug and NP4. Protein analysis indicated that Drug and NP4 had targeted EZH2 and the downstream signaling pathway leading to the decline of EpCAM expression. Conclusions: Targeting EZH2 by Compound 30 has potential use in the treatment of cancer especially hepatocellular carcinoma.

Hit-to-Lead Optimization and Discovery of 5-((5-([1,1′-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase

AMP-activated protein kinase (AMPK) plays an essential role as a cellular energy sensor and master regulator of metabolism in eukaryotes. Dysregulated lipid and carbohydrate metabolism resulting from insulin resistance leads to hyperglycemia, the hallmark of type 2 diabetes mellitus (T2DM). While pharmacological activation of AMPK is anticipated to improve these parameters, the discovery of selective, direct activators has proven challenging. We now describe a hit-to-lead effort resulting in the discovery of a potent and selective class of benzimidazole-based direct AMPK activators, exemplified by 5-((5-([1,1′-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid, 42 (MK-3903). Compound 42 exhibited robust target engagement in mouse liver following oral dosing, leading to improved lipid metabolism and insulin sensitization in mice.

Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents

We herein report the synthesis, biological activity and structure-activity relationship of derivatives of 5,6-dichloro-1-β-d- ribofuranosylbenzimidazole and benzo[d]imidazole. A lead compound 6o demonstrates potent anti-proliferative activity and the ability to induce cancer cell apoptosis.

Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.

Compounds 1-18 have been synthesized and tested in vitro against the protozoa Giardia lamblia, Entamoeba histolytica and the helminth Trichinella spiralis. Inhibition of rat brain tubulin polymerization was also measured and compared for each compound. Results indicate that most of the compounds tested were more active as antiprotozoal agents than Metronidazole and Albendazole. None of the compounds was as active as Albendazole against T. spiralis. Although only compounds 3, 9 and 15 (2-methoxycarbonylamino derivatives) inhibited tubulin polymerization, these were not the most potent antiparasitic compounds.

2H-Benzimidazoles (Isobenzimidazoles). Part 7. A New Route to Triclabendazole and Congeneric Benzimidazoles

A new synthesis of the selective anthelmintic agent triclabendazole 7 from the readily available 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 2 by simple steps is described.Analogous benzimidazoles difficult to prepare by conventional methods are similarly obtained.Triclabendazole can exist as a low-melting metastable solid (m.p. 85-90 deg C) convertible by heating or recrystallisation from ethanol into its stable form (m.p. 176-178 deg C).