174422-17-4

Usage

Uses

Used in Pharmaceutical Development:
2-(4-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid is used as a pharmaceutical precursor for the development of drugs targeting various biological processes. Its anti-cancer properties make it a potential candidate for the treatment of cancer, while its anti-inflammatory and anti-microbial activities suggest potential applications in treating inflammatory and infectious diseases.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-(4-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid serves as a valuable compound for studying its structure-activity relationships and exploring its potential as a lead compound for drug discovery. Its diverse biological activities provide a foundation for further research into its mechanisms of action and optimization for specific therapeutic applications.
Used in Drug Delivery Systems:
To enhance the bioavailability, delivery, and therapeutic efficacy of 2-(4-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid, it can be incorporated into various drug delivery systems. These systems may include nanoparticles, liposomes, or other carriers designed to improve the compound's pharmacokinetics and pharmacodynamics, allowing for more effective treatment of the targeted conditions.
Used in Anticancer Applications:
2-(4-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid is used as an anticancer agent for its potential to target and inhibit the growth of cancer cells. Its anti-cancer properties may be leveraged in the development of novel therapeutics for the treatment of various types of cancer, offering new options for patients and healthcare providers.
Used in Anti-inflammatory and Anti-microbial Applications:
In addition to its anti-cancer potential, 2-(4-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid also exhibits anti-inflammatory and anti-microbial activities. It can be used as a therapeutic agent in the treatment of inflammatory conditions and infections, providing an alternative or complementary approach to existing treatments.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 619-05-6 3,4-diaminobenzoic acid 
• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 36692-49-6 Methyl 3,4-diaminobenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 135-02-4 ortho-anisaldehyde 
• 33402-67-4 sodium hydroxy(4-methoxyphenyl)methanesulfonate 

Downstream Products

• 747356-47-4 2-(4-Methoxy-phenyl)-1H-benzoimidazole-5-carbonyl chloride 
• 1259500-80-5 4''-O-(2-(4-methoxyphenyl)-1H-benzimidazole-5-carbonyl)hydrazinecarbonylclarithromycin 

Relevant academic research and scientific papers

Structure-Guided Synthesis and Evaluation of Small-Molecule Inhibitors Targeting Protein–Protein Interactions of BRCA1 tBRCT Domain

The tandem BRCT domains (tBRCT) of BRCA1 engage phosphoserine-containing motifs in target proteins to propagate intracellular signals initiated by DNA damage, thereby controlling cell cycle arrest and DNA repair. Recently, we identified Bractoppin, the fi

Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media

Various substituted benzimidazoles have been successfully synthesized in aqueous medium by developing VO(acac)2–Cu(OTf)2 catalytic system. A green synthetic protocol has been created in presence of water and cetyltrimethyl ammonium bromide (CTAB) system in an organic solvent free condition. This chemoselective cyclocondensation cumoxidation process occurred in aqueous media. In this suitable method easily synthesized 2-Substituted benzimidazoles with good yields and no 1,2-disubstituted by-products were noticed. Excellent yields, environmentally benign and mild reaction condition, easy purification of the desired products are the main attractive features of this newly devised method.

NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

Novel clarithromycin analogs with C-4′′ 2-arylbenzimidazolyl bishydrazide side chain: Synthesis and antibacterial evaluation

A series of novel 4′′-O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4′′-O-2- arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4′′ bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.

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.

Synthesis of glycal-based chiral benzimidazoles by VO(acac) 2-CeCl3 combo catalyst and their self-aggregated nanostructured materials

(Figure Presented) VO(acac)2-CeCl3 combo catalyst has been developed for chemoselective cyclocondensation cum oxidation under mild reaction conditions toward synthesis of a new class of optically pure compounds, 2-(2′-C-3′,4′,6′-tri-O-benzyl/methyl-glycal)-1H- benzimidazoles. It involves an operationally simple synthetic protocol efficient for the syntheses of a wide range of chiral benzimidazoles in high yields without formation of undesired 1,2-disubstituted and pseudoglycal byproducts. Vanadium(V) is found as active oxidant for the chemical processes which is investigated by UV absorption spectroscopy. Highly ordered one-dimensional low molecular mass organic nanostructured materials are fabricated by nanocrystallization of the chiral nanoscale building blocks. Theoretical calculation by the B3LYP/6-31G** level of theory of the glycal-based chiral benzimidazoles shows out of planar geometry of the 1H-anthra[1,2-d] imidazole-6,11-dione moiety, which is responsible for the strong self-aggregation to generate ultralong nanostructured materials. We have also found nice agreement between the theoretical results with the experimental observation in 2D-NOESY experiments. The photophysical property of the solid nanostructured materials is also reported. 2009 American Chemical Society.

A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization

A highly efficient and versatile method for the synthesis of benzimidazoles was achieved in one step via the Na2S2O4 reduction of o-nitroanilines in the presence of aldehydes. Heating a solution of o-nitroaniline (Ic) and an aldehyde in EtOH or another appropriate solvent, in the presence of aqueous or solid Na2S2O4, provided facile access to a series of 2-substituted N-H benzimidazoles 5a-m containing a wide range of functional groups not always compatible with the existing synthetic methods. This methodology has also been applied to the regioselective synthesis of N-alkyl and N-aryl benzimidazoles 6a-f via the cyclization of the corresponding N-substituted nitroanilines 13a-e, respectively. In addition, the method was applied successfully to the synthesis of other imidazole containing heterocyclic ring systems such as 1H-imidazo[4,5-b]pyridines 14a,b and 1H-imidazo[4,5-f]quinoline 15.

SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLE-5(6)-CARBOXAMIDES AND EVALUATION OF THEIR ANTIMICROBIAL ACTIVITY

A series of 14,N'-(N,N-dialkylaminoethyl)-benzimidazole-5(6) or 5-carboxamides (1-14), having several substituents on the azole and benzene nuclei, were prepared and evalueted in vitro for antimicrobial activity.The precursor bezimidazolecarboxylic acids (15-27) were prepared via oxidative condensation of diaminobenzoic acids and several aldehydes with cupric ion.Compounds 11-14 were prepared by selective regioisomer synthesis.All carboxamides were prepared from the corresponding acids and N,N-dialkylethylenediamine.Antibacterial and antifungal activities were determined as MICs values.Of the synthesized compounds 1-10, 6 and 10 were found to be most favourable.In order to clarify the effect of the substituents at N1 on antimicrobial activity, 12 was prepared by p-chlorobenzyl substitution of compound 6, and increased activity was shown.Compounds 13 and 14, which were prepared by replacement with more bulky alkyl groups on the tert-N atom than 12, gave the best results.