15788-16-6

Usage

Uses

Used in Chemical Industry:
1H-Benzimidazole-5-carboxylic acid is used as a corrosion inhibitor for strong acids. Its ability to protect materials from the corrosive effects of strong acids makes it a valuable additive in the chemical industry, where it can be employed to extend the lifespan of equipment and reduce maintenance costs.
Used in Pharmaceutical Industry:
1H-Benzimidazole-5-carboxylic acid is used as a building block for the synthesis of various bioactive molecules, such as 1H-benzoimidazole-5-carboxylic acid benzotriazol-1-yl ester and piperidin-1-yl(1-m-tolyl-1H-benzo[d]imidazol-5-yl)methanone. These synthesized compounds have potential applications in the development of new drugs, targeting specific diseases and conditions.
Used in Research and Development:
1H-Benzimidazole-5-carboxylic acid serves as a hapten for the production of drug-specific monoclonal antibodies. These antibodies can be used in research and development to study the interactions between drugs and their target molecules, leading to a better understanding of drug mechanisms and the development of more effective therapeutic agents.

InChI:InChI=1/C8H6N2O2/c11-8(12)5-1-2-6-7(3-5)10-4-9-6/h1-4H,(H,9,10)(H,11,12)

Upstream product

• 614-97-1 5-methylbenzimidazole 
• 26113-31-5 4-formylamino-3-nitro-benzoic acid 
• 64-18-6 formic acid 
• 619-05-6 3,4-diaminobenzoic acid 
• 28533-43-9 4-formamidobenzoic acid 
• 124-38-9 carbon dioxide 
• 4887-88-1 5-bromo-1H-benzo[d]imidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 528-45-0 3,4-dinitrobenzoic acid 
• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 26663-77-4 methyl 1H-benzo[d]imidazole-5-carboxylate 

Downstream Products

• 156674-27-0 1-(4,4'-dipropylbenzhydryl)benzimidazole-6-carboxylic acid 
• 400653-36-3 1-{[(1,1-dimethylethyl)oxy]carbonyl}-1H-benzimidazole-5-carboxylic acid 
• 108038-52-4 1H-benzimidazole-5-carbohydrazide 
• 160882-30-4 1H-benzo[d]imidazole-5-carbonyl chloride 
• 162046-54-0 4-((5-benzimidazolylcarbonyl)amino)phenylacetic acid 
• 875-51-4 4-Bromo-2-nitroaniline 
• 58442-17-4 1H-benzo[d]imidazole-5-carbaldehyde 
• 401791-56-8 phenylmethyl (2S)-2-(benzimidazol-5-ylcarbonylamino)-3-phenylpropanoate 
• 401791-57-9 benzyl (2S)-2-(benzimidazol-5-ylcarbonylamino)-3-(O-acetyl-p-hydroxyphenyl)propanoate 
• 106429-29-2 5-(hydroxymethyl)-benzimidazole 
• 131020-36-5 methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate 
• 115576-91-5 (1-methyl-1H-benzimidazol-5-yl)methanol 
• 1439932-80-5 4'-((5-((1-phenylpropyl)carbamoyl)-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1439932-81-6 4'-((6-((1-phenylpropyl)carbamoyl)-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 

Related news

Discovery, SAR and X-ray structure of 1H-Benzimidazole-5-carboxylic acid (cas 15788-16-6) cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk)09/07/2019

A series of novel potent benzimidazole based inhibitors of interleukin-2 T-cell kinase (Itk) were prepared. In this report, we discuss the structure–activity relationship (SAR), selectivity, and cell-based activity for the series. We also discuss the SAR associated with an X-ray structure of on...detailed

Relevant academic research and scientific papers

Homology modelling, molecular dynamics simulation and docking evaluation of β-tubulin of Schistosoma mansoni

Schistosomiasis is one of the neglected diseases causing considerable morbidity and mortality throughout the world. Microtubules with its main component, tubulin play a vital role in helminthes including schistosomes. Benzimidazoles represent potential drug candidates by binding β-tubulin. The study aimed to generate a homology model for the β-tubulin of S. mansoni using the crystal structure of O vis aries (Sheep) β-tubulin (PDB ID: 3N2G D) as a template, then different β-tubulin models were generated and two previously reported benzimidazole derivatives (NBTP-F and NBTP-OH) were docked to the generated models, the binding results indicated that both S. mansoni, S. haematobium were susceptible to the two NBTP derivatives. Additionally, three mutated versions of S. mansoni β-tubulin wild-type were generated and the mutation (F185Y) seems to slightly enhance the ligand binding. Dynamics simulation experiments showed S. haematobium β-tubulin is highly susceptible to the tested compounds; similar to S. mansoni, moreover, mutated models of S. mansoni β-tubulin altered its NBTPs susceptibility. Moreover, additional seven new benzimidazole derivatives were synthesized and tested by molecular docking on the generated model binding site of S. mansoni β-tubulin and were found to have good interaction inside the pocket.

Synthesis of benzimidazole derivatives using heterogeneous ZnO nanoparticles

A mild and efficient procedure for synthesis of benzimidazole derivatives in the presence of a catalytic amount of mechanochemically synthesized zinc oxide nanoparticles under solvent-free condition has been achieved.

Multi-target inhibitor acting on QC and GSK-3[beta]

The invention discloses a multi-target inhibitor acting on QC and GSK-3[beta], wherein the multi-target inhibitor has the structural general formula shown in the specification; according to active center crystal structures of target QC and GSK-3[beta] zymoprotein, with synthesis of multiple high-activity pharmacophores, the multi-target inhibitor capable of acting on QC and GSK-3[beta] at the sametime is prepared through skeletal transition and recombination design; the multi-target inhibitor is a high-activity molecule with multiple target points, the molecular structure diversity of a leaddrug is remarkably expanded, and research and development of innovative anti-AD drugs and AD diagnostic kits are actively promoted.

Preparation method and application of multi-target inhibitor acting on QC and GSK-3beta

The invention discloses a preparation method and application of a multi-target inhibitor acting on QC and GSK-3 beta. The structural general formula of the multi-target inhibitor prepared by the method is shown in the specification. According to the invention, according to active center crystal structures of target QC and GSK-3 beta zymoprotein, multiple high-activity pharmacophores are integrated, the multi-target inhibitor capable of acting on QC and GSK-3 beta at the same time is prepared through framework transition and recombination design, the multi-target inhibitor is molecules with multiple target points and high activity, the molecular structure diversity of a lead drug is remarkably expanded, and the research and development of innovative anti-AD drugs and AD diagnostic kits areactively promoted, and the preparation method of the multi-target inhibitor provided by the invention is simple and easy to operate.

Halogen–metal exchange on bromoheterocyclics with substituents containing an acidic proton via formation of a magnesium intermediate

A selective and practical bromine–metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination of i-PrMgCl and n-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen–lithium exchange, but also offered a highly selective method for performing bromo–metal exchange on dibrominated arene compounds through chelation effect.

Carbon Dioxide Mediated Novel Synthesis of Quinazoline-2,4(1H,3H)-dione in Water

A novel, efficient, and scalable CO2 mediated synthesis of quinazoline-2,4(1H,3H)-dione was developed by a simple cyclization of 2-aminobenzonitrile with DMF in water as the solvent. This is the first report of its kind. DMF was used as the necessary carbon source in the synthesis of quinazoline-2,4(1H,3H)-dione. This synthetic protocol is very efficient; it gives >99% conversion with excellent selectivity. The product was isolated by filtration because of the highly insoluble nature of quinazoline-2,4(1H,3H)-dione in water. The co-product, dimethyl amine, also has industrial importance, and the CO2 that is used can be recycled. This protocol has wide-spread applications in the syntheses of benzimidazole and benzothiazole.

Synthesis method of Ramosetron

The invention discloses a synthesis method of Ramosetron. According to the method, 3,4-diaminobenzoic acid is used as a starting raw material for finally preparing the Ramosetron through the synthesis of benzimidazole-5-carboxylic acid, benzimidazole-5-methyl carbonate sulfate, 4,5,6,7-tetrahydro benzimidazole-5-methyl carbonate sulfate, 4,5,6,7-tetrahydro benzimidazole-5-triazolylformate sulfate, N-[(4,5,6,7-tetrahydro benzimidazole-5-yl)] pyrrole hydrochloride and 5-[(1-methylindol -3-yl) carbonyl]-4,5,6,7-tetrahydro benzimidazole. Compared with the prior art, the method provided by the invention has the advantages that the reaction conditions are optimized; after the optimization, the reaction is really feasible; the yield of the 4,5,6,7-tetrahydro benzimidazole-5-methyl carbonate sulfate, the 4,5,6,7-tetrahydro benzimidazole-5-triazolylformate sulfate, the N-[(4,5,6,7-tetrahydro benzimidazole-5-yl)] pyrrole hydrochloride and the like is improved; the reaction total yield reaches more than 30 percent; higher economic benefits are realized.

Gold-Catalyzed Reductive Transformation of Nitro Compounds Using Formic Acid: Mild, Efficient, and Versatile

Developing new efficient catalytic systems to convert abundant and renewable feedstocks into valuable products in a compact, flexible, and target-specific manner is of high importance in modern synthetic chemistry. Here, we describe a versatile set of mild catalytic conditions utilizing a single gold-based solid catalyst that enables the direct and additive-free preparation of four distinct and important amine derivatives (amines, formamides, benzimidazoles, and dimethlyated amines) from readily available formic acid (FA) and nitro starting materials with high level of chemoselectivity. By controlling the stoichiometry of the employed FA, which has attracted considerable interest in the area of sustainable chemistry because of its potential as an entirely renewable hydrogen carrier and as a versatile C1 source, a facile atom- and step-efficient transformation of nitro compounds can be realized in a modular fashion. Renewable formic acid as a flexible feedstock: A versatile heterogeneous gold-based catalytic system has been developed for the controlled, flexible, and target-specific reductive transformation of nitro compounds using stoichiometric equivalents of formic acid as a key starting material under mild and convenient conditions. The overall operational simplicity, high chemoselectivity, functional-group tolerance, and reusability of the catalyst make this approach an attractive and reliable tool for organic and process chemists.

SELECTIVE HDAC3 INHIBITORS

Provided herein are HDAC3 inhibitors, as well as methods of treatment comprising administering these compounds to a subject in need thereof.

Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

Novel 4″-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4″ bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the mef gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4″-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4″-O-(2-alkyl)benzimidazolyl derivatives.