180508-09-2

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-4-METHYLBENZIMIDAZOLE is used as a building block for the synthesis of various pharmaceuticals, primarily in the production of anti-ulcer medications. Its unique structure contributes to the development of drugs that can effectively treat ulcers and related gastrointestinal conditions.
Used in Agrochemical Industry:
Although not explicitly mentioned in the provided materials, given its role as a building block in synthesis, 6-CHLORO-4-METHYLBENZIMIDAZOLE may also be utilized in the agrochemical industry for the development of pesticides or other agricultural chemicals, leveraging its chemical properties to target specific pests or enhance crop protection.

InChI:InChI=1/C8H7ClN2/c1-5-2-6(9)3-7-8(5)11-4-10-7/h2-4H,1H3,(H,10,11)

Upstream product

• 64-18-6 formic acid 
• 109671-52-5 2-amino-5-chloro-3-methylaniline 

Downstream Products

• 180569-27-1 6-chlorobenzimidazole-4-carboxylic acid 
• 197860-59-6 6-chloro-7-nitro-1H-benzoimidazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide 
• 197860-62-1 6-chloro-7-nitro-1H-benzoimidazole-4-carboxylic acid 

Relevant academic research and scientific papers

Novel benzimidazole-4-carboxylic acid derivatives as potent and selective 5-HT3 receptor ligands

A series of benzimidazole-4-carboxylic acid derivatives was synthesized and evaluated for affinity at 5-HT3 and 5-HT4 serotoninergic receptors. Compounds 1b, c and j exhibited high affinity for the 5-HT3 receptors (K(i)=6.1, 3.7 and 4.9 nM, respectively) and no significant affinity for 5- HT4 (K(i)>1000 nM) and 5-HT(1A) (K(i)>10 000 nM) sites. Preliminary studies showed that 1c displayed activity in the two-compartment behavioural model.

Benzimidazole derivatives. Part 1: Synthesis and structure-activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

New benzimidazole-4-carboxamides 1-16 and -carboxylates 17-26 were synthesized and evaluated for binding affinity at serotonergic 5-HT4 and 5- HT3 receptors in the CNS. Most of the synthesized compounds exhibited moderate-to-very high affinity (in many cases subnanomolar) for the 5-HT4 binding site and no significant affinity for the 5-HT3 receptor. SAR observations and structural analyses (molecular modeling, INSIGHT II) indicated that the presence of a voluminous substituent in the basic nitrogen atom of the amino moiety and a distance of ca. 8.0 A from this nitrogen to the aromatic ring are of great importance for high affinity and selectivity for 5-HT4 receptors. These results confirm our recently proposed model for recognition by the 5-HT4 binding site. Amides 12-15 and esters 24 and 25 bound at central 5-HT4 sites with very high affinity (K(i) = 0.11-2.9 nM) and excellent selectivity over serotonin 5-HT3, 5-HT(2A), and 5-HT(1A) receptors (K(i) > 1000-10,000 nM). Analogues 12 (K(i)(5-HT4) = 0.32 nM), 13 (K(i)(5-HT4) = 0.11 nM), 14 (K(i)(5-HT4) = 0.29 nM) and 15 (K(i)(5-HT4) = 0.54 nM) were pharmacologically characterized as selective 5-HT4 antagonists in the isolated guinea pig ileum (pA2 = 7.6, 7.9, 8.2 and 7.9, respectively), with a potency comparable to the 5-HT4 receptor antagonist RS 39604 (pA2 = 8.2). The benzimidazole-4-carboxylic acid derivatives described in this paper represent a novel class of potent and selective 5-HT4 receptor antagonists. In particular, compounds 12-15 could be interesting pharmacological tools for the understanding of the role of 5-HT4 receptors. (C) 1999 Elsevier Science Ltd.