52329-60-9

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-BENZOYL-BENZIMIDAZOLE is used as a novel heterocyclic NF-κB inhibitor for its ability to modulate cellular signaling pathways. This property makes it a valuable component in the development of pharmaceutical compositions targeting various diseases and conditions.
Used in Anticancer Applications:
In the field of oncology, 2-AMINO-5-BENZOYL-BENZIMIDAZOLE is used as a potential anticancer agent. Its NF-κB inhibitory activity can help in the development of treatments for various types of cancer by targeting the underlying molecular mechanisms involved in tumor growth and progression.
Used in Drug Development:
As a minor urinary metabolite of Mebendazole (M200500) in humans, 2-AMINO-5-BENZOYL-BENZIMIDAZOLE can be utilized in the study and development of new drugs, particularly those targeting parasitic infections. Understanding its metabolic pathways and interactions can contribute to the design of more effective and safer therapeutic agents.
Used in Drug Impurity Analysis:
2-AMINO-5-BENZOYL-BENZIMIDAZOLE is also used as an impurity in the analysis and quality control of Mebendazole, a widely used anthelmintic drug. Its identification and quantification in drug products can help ensure the safety, efficacy, and quality of the final drug formulation.

Safety Profile

Acute poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. See also KETONES. A flammable liquid. When heated to decomposition it emits very toxic fumes of NOx,.

InChI:InChI=1/C14H11N3O/c15-14-16-11-7-6-10(8-12(11)17-14)13(18)9-4-2-1-3-5-9/h1-8H,(H3,15,16,17)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 31431-39-7 mebendazole 
• 111-41-1 2-(2-Aminoethylamino)ethanol 
• 39070-63-8 4-benzoylbenzene-1,2-diamine 
• 92685-57-9 (2-mercapto-1H-benzo[d]imidazol-6-yl)(phenyl)methanone 
• 929960-88-3 5-benzoyl-1H-benzimidazole-2-sulfonic acid 
• 57070-71-0 (3,4-diaminophenyl)phenylmethanone hydrochloride 
• 872279-54-4 3-amino-4-bromo-benzophenone 
• 77287-34-4 formamide 
• 31431-39-7 mebendazole 
• 108227-94-7 N-(2-Amino-5-benzoyl-phenyl)-guanidine 
• 506-68-3 bromocyane 
• 141-43-5 ethanolamine 
• 108227-96-9 Amino-5-benzoylbenzimidazole-hydrochlorid 

Downstream Products

• 120573-37-7 2-(5-Benzoyl-1H-benzoimidazol-2-ylamino)-1-(3-methyl-piperidin-1-yl)-ethanone 
• 89597-92-2 1-(5-Benzoyl-1H-benzoimidazol-2-yl)-3-(3-nitro-phenyl)-urea 
• 75501-05-2 2-amino-5(6)-(α-hydroxy-α-phenylmethyl)benzimidazole 
• 89597-87-5 1-(5-Benzoyl-1H-benzoimidazol-2-yl)-3-m-tolyl-urea 
• 89597-91-1 1-(5-Benzoyl-1H-benzoimidazol-2-yl)-3-(2-nitro-phenyl)-urea 
• 89597-86-4 1-(5-Benzoyl-1H-benzoimidazol-2-yl)-3-p-tolyl-urea 
• 89597-83-1 1-(5-Benzoyl-1H-benzoimidazol-2-yl)-3-methyl-urea 
• 89597-90-0 1-(5-Benzoyl-1H-benzoimidazol-2-yl)-3-(3,4-dichloro-phenyl)-urea 
• 129165-82-8 N,N'-di(5-benzoylbenzimidazol-2-yl)urea 
• 63197-61-5 1-isopropylsulfonyl-2-amino-6-benzoylbenzimidazole 

Relevant academic research and scientific papers

Cobalt-Catalyzed Aerobic Oxidative Cyclization of 2-Aminoanilines with Isonitriles: Facile Access to 2-Aminobenzimidazoles

A ligand- and additive-free aerobic cobalt-catalyzed synthesis of 2-aminobenzimidazoles from 2-aminoanilines was developed. A variety of aminoanilines and isonitriles undergo efficient coupling to furnish substituted 2-aminobenzimidazoles in moderate to excellent yields. This protocol enables efficient access to the unsubstituted 2-aminobenzimidazoles.

Synthesis of benzimidazoles by Cul-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde in water

An efficient copper-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde for the synthesis of benzimidazoles with 1,10-phenanthroline as the ligand has been developed. A variety of substituted benzimidazole derivatives can be obtained in yields up to 95%.

Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles

Two groups of benzimidazole derivatives were synthesized using as precursors 5(6)-substituted 2-mercapto-benzimidazol-thiols and their antioxidant activity was investigated using TBA-MDA test. In the group of 1,3-disubstituted-benzimidazol-2-imines the highest lipid peroxidation inhibition effect 74.04% (IC50 = 141.89 μg/mL) revealed ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimdazol-1-yl]acetate 12 while in the group of 2-substituted-1,3-thiazolo[3,2-a]benzimidazolones the highest inhibition effect showed 2-(4-fluorobenzylidene)-7-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 17 90.76% (IC50 = 53.70 μg/mL). In order to estimate the capability of the studied benzimidazoles to act as radical scavengers the structure of the most active derivative within the both subseries was optimized at B3LYP/6-311++G?? level and the respective bond dissociation enthalpies were calculated. The appropriate models for the HAT and SET-mechanism of the antioxidant activity were proposed. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and three Gram-negative bacteria (Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027 and Salmonella abony NCTC 6017). 1,3-Diphenylpropyl-5-methyl-1,3-dihydro-2H-benzimidazol-2-imine 14 exhibited significant activity against B. subtilis, S. aureus, S. abony and E. coli (with MIC values of 0.125, 0.016, 0.50 and 0.50 mg/mL, respectively). The group of thiazolobenzimidazolones did not reveal antibacterial activity against the tested strains.

Design, synthesis and antiproliferative properties of some new 5-substituted-2-iminobenzimidazole derivatives

Some new 1,3,5-substituted-2,3-dihydro-2-imino-benzimidazoles were synthesized under solid-liquid phase transfer catalysis conditions using 5-substituted-2-aminobenzimidazoles as precursors in order to assess their cytotoxicity respectively proliferative activity. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. Compounds 9-10, 12 and 16-17 were evaluated for their cytotoxical effect on four cancer cell lines: HT-29, breast cancer cells MDA-MB-231, HeLa, HepG2 and as well as human diploid cell line Lep-3. Significant cytotoxicity of hydrazone 16 against MDA-MB-231 was established by biologically study, the IC50 was 6.2 nM while the EC50 value to Lep 3 is 0.21 nM. Relative high antiproliferative effects of the acetate 12 and compound 16 against HT-29 were ascertained and the calculated IC50 values were IC50 - 0.85 nM and IC50 - 2.83 nM respectively. Cytotoxic activity against HeLa and HepG2 cells was demonstrated by hydrazone 17, IC50 was 7.2 nM and 117 nM respectively. All tested compounds revealed proliferative activities to human diploid cell line Lep-3. The EC50 values were in the range from 0.05 to 16.91 nM. The obtained results prove the selective cytotoxicity of the tested compounds and are promising for further evaluation of the investigated compounds in vivo experiments using experimentally induced tumors in laboratory animals.

Inhibition and Dispersion of Bacterial Biofilms with 2-Aminobenzimidazole Derivatives

Compounds described herein inhibit biofilm formation or disperse pre-formed biofilms of Gram-negative bacteria. Biofilm-inhibitory compounds can be encapsulated or contained in a polymer matrix for controlled release. Coatings, films, multilayer films, hydrogels, microspheres and nanospheres as well as pharmaceutical compositions and disinfecting compositions containing biofilm-inhibitory compounds are also provided. Methods for inhibiting formation of biofilms or dispersing already formed biofilms are provided. Methods for treating infections of gram-negative bacteria which form biofilms, particularly those of Pseudomonas and more particularly P. aeruginosa.

Benzoylbenzimidazole-based selective inhibitors targeting Cryptosporidium parvum and Toxoplasma gondii calcium-dependent protein kinase-1

Calcium-dependent protein kinase-1 (CDPK1) from Cryptosporidium parvum (CpCDPK1) and Toxoplasma gondii (TgCDPK1) have become attractive targets for discovering selective inhibitors to combat infections caused by these protozoa. We used structure-based design to improve a series of benzoylbenzimidazole-based compounds in terms of solubility, selectivity, and potency against CpCDPK1 and TgCDPK1. The best inhibitors show inhibitory potencies below 50 nM and selectivity well above 200-fold over two human kinases with small gatekeeper residues.

2-aminobenzimidazole derivatives strongly inhibit and disperse Pseudomonas aeruginosa biofilms

Bacterial biofilms are exceptionally difficult to clear using traditional antibiotics and constitute a significant health threat. 2-Aminobenzimidazole derivatives (see scheme) are capable of strongly inhibiting the growth of and dispersing Pseudomonas aeruginosa biofilms. These molecules were found to modulate quorum sensing in reporter strains, and represent some of strongest P. aeruginosa biofilm inhibitors known. Copyright

Studies in antiparasitic agents: Part 20 - Synthesis of probenzimidazoles, benzimidazoles and purimidobenzimidazoles as possible anthelmintics

A series of tetrasubstituted benzophenones (1-35) have been synthesized as probenzimidazoles.Some 2,5-disubstituted benzimidazoles (36-39 and 43-61) and pyrimidobenzimidazoles (40-42) have also been prepared.Of these compounds 4, 5, 15, 27, 29, 30, and 51 exhibit 100percent antihookworm activity against A. ceylanicum in hamsters at an oral dose of 250 mg/kg*3 while compounds 3, 4, 26-30 cause 100percent elimination of tapeworms, H. nana at a dose of 250 mg/kg.Compound 4 kills 90percent of the microfilariae of L. carinii at an intraperitoneal dose of 30 mg/kg*5.Another compound, 48 shows 6 4-78percent microfilaricidal and 38-62percent macrofilaricidal action against L. carinii and B. malayi at a dose of 50 mg/kg*5.

Receptor-based design of novel dihydrofolate reductase inhibitors: Benzimidazole and indole derivatives

Although many thousands of inhibitors of the enzyme dihydrofolate reductase (DHFR) have been synthesized, all of the very active compounds have been 2,4-diaminopyrimidines or very close analogues. This paper describes 2,4-diamino-6-benzylbenzimidazole (3b