174422-16-3

Basic information

• Product Name: 2-(2-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid
• Synonyms: 2-(2-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid
• CAS NO: 174422-16-3
• Molecular Formula: C₁₅H₁₂N₂O₃
• Molecular Weight: 268.27
• Mol File: 174422-16-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid(174422-16-3)
• EPA Substance Registry System: 2-(2-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid(174422-16-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 174422-16-3(Hazardous Substances Data)

Usage

Benzimidazole derivative

The compound is derived from benzimidazole, which is a heterocyclic aromatic organic compound known for its importance in medicinal chemistry.

Carboxylic acid group

The presence of a carboxylic acid group (-COOH) in the compound contributes to its acidity and may play a role in its biological activity.

Methoxyphenyl group

The compound also contains a methoxyphenyl group (-OCH3), which is a phenyl ring with a methoxy substituent. This group can influence the compound's solubility, stability, and interaction with biological targets.

Potential applications in medicine and pharmacology

Due to its structural features and potential biological activities, 2-(2-Methoxyphenyl)-1H-benzimidazole-5-carboxylic acid may have uses in drug development and therapeutic purposes.

Interaction with biological targets

The compound may interact with specific biological targets, such as proteins or enzymes, which could lead to potential therapeutic effects.

Need for further research

More studies are required to explore the compound's potential uses and biological effects, as its full potential is not yet fully understood.

Upstream product

• 135-02-4 ortho-anisaldehyde 
• 619-05-6 3,4-diaminobenzoic acid 

Downstream Products

• 1259500-81-6 4''-O-(2-(2-methoxyphenyl)-1H-benzimidazole-5-carbonyl)hydrazinecarbonylclarithromycin 

Relevant articles and documents

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 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.