39791-96-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5,6-dimethylbenzimidazole is used as an intermediate in the synthesis of various pharmaceuticals for its antimicrobial and antifungal properties. It contributes to the development of medicinal products that target a wide range of infections and diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Chloro-5,6-dimethylbenzimidazole is utilized as an intermediate in the production of agrochemicals. Its antimicrobial and antifungal properties make it an essential component in creating products that protect crops from various pathogens and pests, thereby ensuring increased agricultural productivity.
Used in Dye Industry:
2-Chloro-5,6-dimethylbenzimidazole is employed as an intermediate in the synthesis of dyes due to its chemical properties. It plays a significant role in the development of dyes with specific color characteristics and properties, catering to various applications in different industries such as textiles, plastics, and printing inks.

InChI:InChI=1/C9H9ClN2/c1-5-3-7-8(4-6(5)2)12-9(10)11-7/h3-4H,1-2H3,(H,11,12)

Upstream product

• 29096-75-1 2-amino-5,6-dimethylbenzimidazole 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 2033-30-9 NSC 163165 

Relevant academic research and scientific papers

Discovery and Structure-Based Optimization of Benzimidazole-Derived Activators of SOS1-Mediated Nucleotide Exchange on RAS

Son of sevenless homologue 1 (SOS1) is a guanine nucleotide exchange factor that catalyzes the exchange of GDP for GTP on RAS. In its active form, GTP-bound RAS is responsible for numerous critical cellular processes. Aberrant RAS activity is involved in ～30% of all human cancers; hence, SOS1 is an attractive therapeutic target for its role in modulating RAS activation. Here, we describe a new series of benzimidazole-derived SOS1 agonists. Using structure-guided design, we discovered small molecules that increase nucleotide exchange on RAS in vitro at submicromolar concentrations, bind to SOS1 with low double-digit nanomolar affinity, rapidly enhance cellular RAS-GTP levels, and invoke biphasic signaling changes in phosphorylation of ERK 1/2. These compounds represent the most potent series of SOS1 agonists reported to date.

PIPERIDINYL BENZOIMIDAZOLE DERIVATIVES AS MPGES-1 INIHIBITORS

A compound of formula (I) as well as pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the compound. The compound is useful for the treatment of disorder selected from inflammatory diseases, pain, auto-immune disease, breathing disorders, fever, cancer, inflammation related anorexia, overactive bladder, familial adenomatous polyposis (FAP) condition, neurodegenerative diseases, bone diseases and cardiovascular diseases.

MICROSOMAL PROSTAGLANDIN E SYNTHASE-1 (MPGES1) INHIBITORS

A compound of formula (I): as well as pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the compound. The compound is useful for the treatment of disorder selected from inflammatory diseases, nociceptive pain, auto-imm

Design, syntheses, and structure-activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright

4-(2-Pyridyl)piperazine-1-benzimidazoles as potent TRPV1 antagonists

A series of 4-(2-pyridyl)piperazine-1-benzimidazole analogues based on compound 1 was synthesized and evaluated for TRPV1 antagonist activity in capsaicin-induced (CAP) and pH 5.5-induced (pH) FLIPR assays in a human TRPV1-expressing HEK293 cell line. Potent TRPV1 antagonists were identified through SAR studies. From these studies, several antagonists were found, with IC50 values ranging from 32 nM to ～5000 nM. Among these, 11 [IC50 = 90 nM (CAP) and 104 nM (pH)] was further evaluated and found to be orally available in rats (F% = 19.7).

New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation

A series of 2-piperazinylbenzimidazole derivatives were prepared and evaluated as 5-HT3 receptor antagonists. Their 5-HT3 receptor affinities were evaluated by radioligand binding assays, and their abilities to inhibit the 5-HT-induced Bezold-Jarisch reflex in anesthetized rats were determined. Compound 7e (lerisetron, pK(i) = 9.2) exhibited higher affinity for the 5- HT3 receptor than did tropisetron and granisetron, while compound 7q (pK(i) = 7.5) had very low affinity for this receptor, showing that substitution on the N1 atom of the benzimidazole ring is essential for affinity and activity. The effect of substitution on the aromatic ring of benzimidazole by several substituents in different positions is also discussed. A strong correlation between the 5-HT3 antagonistic activity of the studied compounds and the position of substitution on the aromatic ring was established. Thus, while the 4-methoxy derivative 7m showed weak affinity for the 5-HT3 receptor (pK(i) = 6.7), the 7-methoxy derivative 7n exhibited the highest affinity (pK(i) = 9.4). Compounds 7e and 7n are now under further investigation as drugs for the treatment of nausea and emesis evoked by cancer chemotherapy and radiation.