5805-42-5

Usage

Derivative of benzimidazole

A heterocyclic compound commonly found in pharmaceuticals and agrochemicals

Substitution on benzimidazole ring

2-ethyl and 5-nitro

Use as a building block

In the synthesis of various pharmaceuticals and agrochemicals

Unique chemical properties

Contribute to its use in synthesis

Potential biological activities

Antimicrobial and antitumor properties

Valuable tool

In the development of new drugs and agricultural products

InChI:InChI=1/C9H9N3O2/c1-2-9-10-7-4-3-6(12(13)14)5-8(7)11-9/h3-5H,2H2,1H3,(H,10,11)

Upstream product

• 1848-84-6 2-ethylbenzimidazole 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 115-80-0 Triethyl orthopropionate 
• 71-23-8 propan-1-ol 
• 95-54-5 1,2-diamino-benzene 
• 7424-54-6 3,5-heptanedione 
• 802294-64-0 propionic acid 
• 79-03-8 propionyl chloride 
• 7470-53-3 N-(2,4-dinitro-phenyl)-propionamide 
• 97-02-9 2,4-Dinitroanilin 
• 849435-63-8 N-(2-amino-4-nitro-phenyl)-propionamide 
• 40546-35-8 ethyl propanimidate hydrochloride 
• 88374-33-8 N-(2-amino-5-nitrophenyl)propionamide 

Downstream Products

• 1352942-37-0 2-ethyl-5-(phthaloyl-L-phenylalanyl)-amino benzimidazole 
• 1352942-43-8 2-ethyl-5-(L-phenylalanyl)-amino benzimidazole 
• 46055-62-3 2-ethyl-1H-benzo[d]imidazol-5-amine 
• 1596263-76-1 2-(4-((2-ethyl-5-nitro-1H-benzo[d]imidazol-1-yl)methyl)-1H-indol-1-yl)benzonitrile 
• 1443665-57-3 2-(4-((2-ethyl-5-nitro-1H-benzo[d]imidazol-1-yl)methyl)-1H-indol-1-yl)benzoic acid 

Relevant academic research and scientific papers

Synthesis, characterization, antitumor, antibacterial and urease inhibitory activity of a small series of N-tosyl benzimidazoles

Benzimidazole derivatives exhibited a broad range of biological activities, e.g., antimicrobial, antiviral, anthelmintic, anti-inflammatory, anticancer and as an anti-ulcer/proton pump inhibitor. Keeping in view the large number of reported drugs containing benzimidazole moiety on one hand and sulfonamide on the other hand, a small series of N-tosyl benzimidazoles (4a-e) have been synthesized. The present work describes the synthesis, characterization and bio-evaluation of five new N-tosyl benzimidazoles with the objective to develop new compounds with improved anticancer, antibacterial and urease inhibitory activities. The substituted 1,2-phenylenediamines in the first step were condensed with aliphatic carboxylic acids to synthesize the substituted benzimidazoles. In the second step the tosyl chloride was reacted with substituted benzimidazoles in basic conditions to afford the title N-tosyl benzimidazoles (4a-e). The screening for their antitumor activities was performed against Agrobacterium tumefaciens by following the potato disc tumor assay. The compound (4e) exhibited excellent antitumor activity with IC50 values 474.45μgml-1 compared to other synthesized compounds. Antibacterial activity results revealed that compounds 4d and 4e having methyl and ethyl substitution respectively at the imidazole ring showed excellent zone inhibition against both gram positive and gram negative strains. The urease inhibitory activity results showed that derivative 4e exhibited highest potential to inhibit the urease enzyme compared to all other derivatives. Based upon our investigation it is proposed that compound (4e) may serve as lead structure to design more potent biological active compounds having multitargets inhibition activities.

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Discovery of [5-Amino-1-(2-methyl-3H-benzimidazol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone (CH5183284/Debio 1347), An Orally Available and Selective Fibroblast Growth Factor Receptor (FGFR) Inhibitor

The fibroblast growth factor receptor (FGFR) family of receptor tyrosine kinases regulates multiple biological processes, such as cell proliferation, migration, apoptosis, and differentiation. Various genetic alterations that drive activation of the recep

Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

Convenient synthesis of benzothiazoles and benzimidazoles through bronsted acid catalyzed cyclization of 2-amino thiophenols/anilines with β-diketones

Bronsted acid catalyzed cyclization reactions of 2-amino thiophenols/anilines with β-diketones under oxidant-, metal-, and radiation-free conditions are described. Various 2-substituted benzothiazoles/benzimidazoles are obtained in satisfactory to excellent yields. Different groups such as methyl, chloro, nitro, and methoxy linked on benzene rings were tolerated under the optimized reaction conditions.

Design, synthesis and biological evaluation of new 5-nitro benzimidazole derivatives as AT1 antagonists with anti-hypertension activities

The design, synthesis, in vitro and in vivo evaluation of 5-nitro benzimidazole with 1,4-disubsituted or 1,5-disubsituted indole derivatives as novel angiotensin II receptor antagonist is outlined. Radioligand binding assays showed that 2-(4-((2-butyl-5-n

New antibacterial diazotized derivatives of 5-amino azaheterocycles

Six new diazotized derivatives of pharmacologically important azaheterocycles (2a-d, 4a-b) were prepared from their corresponding 5-amino benzimidazoles (1a-d) and benzimidazolones (3a-b). All new compounds have been characterized on the basis of their IR, NMR and Mass spectral data. Antibacterial activity of these compounds is also been reported.

Microwave-assisted synthesis of some novel benzimidazole compounds containing oxadiazole moiety

5(6)-Nitro-2-alkyl/aryl-1H-benzimidazoles were obtained from the reaction of iminoester hydrochlorides and 4-nitro-ophenylenediamine, and converted to their ester and hydrazide derivatives. Hydrazide derivatives were used as a key intermediate to prepare 5-[(2-alkly/arly-5(6)-nitro-1H-benzimidazol-1-yl) methyl]-1, 3, 4-oxadiazol-2-thioles.

Tungstate sulfuric acid: Preparation, characterization, and application in catalytic synthesis of novel benzimidazoles

Tungstate sulfuric acid (TSA) was prepared, characterized, and applied for direct synthesis of novel and known benzimidazoles through a condensation reaction of o-phenylenediamines with orthoesters under solvent-free conditions. TSA was characterized by powdered X-ray diffraction (XRD), X-ray fluorescence (XRF), and FTIR spectroscopy. This novel and eco-friendly method is very cheap and has many advantages such as excellent yields, recyclable and eco-friendly catalyst, and simple work-up procedure.

Novel approach to benzimidazoles using Fe3O4 nanoparticles as a magnetically recoverable catalyst

Magnetically recoverable Fe3O4 nanoparticles have been synthesized as a catalyst for the cyclocondensation of 1,2- phenylenediamines with orthoesters under solvent-free conditions. Catalyst loadings can be as low as 1 mol to give high yields of the corresponding benzimidazole derivative at 80°C. This green method offers significant advantages in terms of its simplicity, low catalyst loadings, high product yields, and non-toxic nature. The Fe3O4 nanoparticles were characterized by X-ray diffraction, transmission electron microscopy, and Fourier transform infrared spectroscopy.