29096-75-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5,6-dimethylbenzimidazole is used as a chemical intermediate for the synthesis of various drugs due to its unique structure and functional groups.
Used in Antineoplastic Applications:
2-Amino-5,6-dimethylbenzimidazole is used as an antineoplastic agent for its potential to combat cancer by interfering with the growth and proliferation of cancer cells.
Used in Antiviral Applications:
2-Amino-5,6-dimethylbenzimidazole is used as an antiviral agent for its potential to inhibit the replication and spread of viruses within the body.
Used in Anti-inflammatory Applications:
2-Amino-5,6-dimethylbenzimidazole is used as an anti-inflammatory agent for its potential to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Antimicrobial Applications:
2-Amino-5,6-dimethylbenzimidazole is used as an antimicrobial agent for its potential to combat microbial infections by inhibiting the growth of bacteria and other microorganisms.
Used in Disease Treatment Research:
2-Amino-5,6-dimethylbenzimidazole is used in pharmaceutical research for its potential in the treatment of various diseases, making it a valuable chemical in drug development and therapeutic innovation.

InChI:InChI=1/C9H11N3/c1-5-3-7-8(4-6(5)2)12-9(10)11-7/h3-4H,1-2H3,(H3,10,11,12)

Upstream product

• 506-68-3 bromocyane 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 

Downstream Products

• 105958-35-8 C₃₂H₂₆N₃⁽¹⁺⁾*BF₄^(1-) 
• 109929-41-1 7,8-Dimethyl-2,4-diphenyl-benzo[4,5]imidazo[1,2-a]pyrimidine 
• 123199-80-4 N-(5,6-dimethylbenzimidazol-2-yl)salicylamide 
• 60882-73-7 5,6-dimethyl-1,2-diaminobenzimidazole 
• 141472-57-3 [5,6-Dimethyl-1-(3-methyl-benzyl)-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-58-4 [5,6-Dimethyl-1-(2-methyl-benzyl)-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-56-2 [5,6-Dimethyl-1-(4-methyl-benzyl)-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-68-6 [1-(2-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-60-8 [1-(3-Fluoro-benzyl)-5,6-dimethyl-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-67-5 [1-(3-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-59-5 [1-(3-Methoxy-benzyl)-5,6-dimethyl-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 141472-66-4 [1-(4-Chloro-benzyl)-5,6-dimethyl-1H-benzoimidazol-2-yl]-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 1228507-42-3 N-(5,6-dimethyl-1H-benzimidazol-2-yl)-3,5-bis(trifluoromethyl)benzamide 
• 1228507-44-5 N-(5,6-dimethyl-1H-benzimidazol-2-yl)-3-methoxybenzamide 

Relevant academic research and scientific papers

Potentiation of Francisella resistance to conventional antibiotics through small molecule adjuvants

A screen of 20 compounds identified small molecule adjuvants capable of potentiating antibiotic activity against Francisella philomiragia. Analogue synthesis of an initial hit compound led to the discovery of a potentially new class of small molecule adjuvants containing an indole core. The lead compound was able to lower the MIC of colistin by 32-fold against intrinsically resistant F. philomiragia.

Design, synthesis and biological evaluation of 1,2,3-triazole based 2-aminobenzimidazoles as novel inhibitors of LasR dependent quorum sensing in: Pseudomonas aeruginosa

Bacteria regulate their phenotype, growth and population via a signalling pathway known as quorum sensing. In this process, bacteria produce signalling molecules (autoinducers) to recognize their population density. Inhibiting this quorum sensing signalling pathway is one of the potential methods to treat bacterial infection. 2-Aminobenimdazoles are reported to be the strongest inhibitors of quorum sensing against wild-type P. aeruginosa. 1,2,3-Triazole based acyl homoserine lactones are found to be good inhibitors of the quorum sensing LasR receptor. Hence, in our current study, forty 1,2,3-triazole based 2-aminobenzimdazoles were synthesized and characterized using IR, NMR, MS and elemental analysis. A single crystal was developed for N-(1H-benzo[d]imidazol-2-yl)-2-(4-nonyl-1H-1,2,3-triazol-1-yl)acetamide (6d). All final compounds were screened for in vitro quorum sensing inhibitory activity against Pseudomonas aeruginosa. The quorum sensing inhibitory activity was determined in the LasR expressing P. aeruginosa MH602 reporter strain by measuring green fluorescent protein production. Among the title compounds, N-(1H-benzo[d]imidazol-2-yl)-2-(4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl)acetamide (6i) exhibited good quorum sensing inhibitory activity of 64.99% at 250 μM. N-(1H-Benzo[d]imidazol-2-yl)-2-(4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)acetamide (6p) exhibited the most promising quorum sensing inhibitory activity with 68.23, 67.10 and 63.67% inhibition at 250, 125 and 62.5 μM, respectively. N-(1H-Benzo[d]imidazol-2-yl)-2-(4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetamide (6o) and N-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2-(4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetamide (7l) also exhibited 64.25% and 65.80% quorum sensing inhibition at 250 μM. Compound 6p, the most active quorum sensing inhibitor, also displayed low cytotoxicity at the tested concentrations (25, 50 and 100 μM) against normal human embryonic kidney cell lines. Finally, a docking study using Schrodinger Glide elucidated the possible putative binding mode of the significantly active compound 6p at the active site of the target LasR receptor (PDB ID: 2UV0).

Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources

A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C-C bond and C-N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot protocol is reported for the first time. This reaction features broad substrate scope, good functional group tolerance, as well as diversified and valuable products.

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.

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

Catalyst-controlled chemoselective arylation of 2-aminobenzimidazoles

What N would you like? The chemoselective and complementary Pd- and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure (see scheme). Copyright

The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii

Multidrug-resistant bacterial infections continue to be a rising global health concern. Herein is described the development of a class of novel 2-aminobenzimidazoles with antibiotic activity. These active 2-aminobenzimidazoles retain their antibiotic activity against several strains of multidrug-resistant Staphylococcus aureus and Acinetobacter baumannii when compared to susceptible strains.

Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4

High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.

Benzimidazole derivatives

Compounds, pharmaceutical compositions and methods are provided that are useful in the treatment of inflammatory and immune-related conditions or disorders. In particular, the invention provides compounds which modulate the expression and/or function of proteins involved in inflammation, immune response regulation and cell proliferation. The subject compounds are 2-amino-imidazole derivatives.

Method of inhibiting the advanced glycosylation of proteins using 1,2-disubstituted-benzimidazoles

The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, composition is disclosed which comprises 1,2-disubstituted benzimidazoles capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.