355022-55-8

Basic information

• Product Name: 2-(3,4-Dimethoxyphenyl)-1H-benzimidazole-5-carboxylic acid
• Synonyms: 2-(3,4-Dimethoxyphenyl)-1H-benzimidazole-5-carboxylic acid;2-(3,4-dimethoxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid
• CAS NO: 355022-55-8
• Molecular Formula: C₁₆H₁₄N₂O₄
• Molecular Weight: 298.29
• Mol File: 355022-55-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 567.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.350±0.06 g/cm3(Predicted)
• PKA: 3.28±0.30(Predicted)
• CAS DataBase Reference: 2-(3,4-Dimethoxyphenyl)-1H-benzimidazole-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-Dimethoxyphenyl)-1H-benzimidazole-5-carboxylic acid(355022-55-8)
• EPA Substance Registry System: 2-(3,4-Dimethoxyphenyl)-1H-benzimidazole-5-carboxylic acid(355022-55-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 355022-55-8(Hazardous Substances Data)

Usage

Benzimidazole derivative

A compound based on the benzimidazole structure This indicates that the compound is derived from the benzimidazole core structure, which is a significant structural motif in many biologically active molecules.

Carboxylic acid group

Presence of a -COOH functional group This suggests that the compound has acidic properties and may form salts or esters with various cations and alcohols, respectively.

Potential biological activities

Anti-cancer, anti-inflammatory, and anti-bacterial properties These are the possible therapeutic effects that the compound may exhibit, making it a potential candidate for the development of new drugs to treat various diseases and conditions.

Drug candidate

Being studied for its potential as a pharmaceutical agent for various medical conditions This highlights the compound's potential for further research and development in the pharmaceutical industry.

Strong interactions with biological targets

Due to the presence of benzimidazole and carboxylic acid functionalities in its structure This suggests that the compound may have a high affinity for specific biological targets, which could contribute to its therapeutic effects and make it a promising candidate for further research.

Upstream product

• 68413-92-3 sodium (3,4-dimethoxyphenyl)(hydroxy)methanesulfonate 
• 619-05-6 3,4-diaminobenzoic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Relevant articles and documents

Synthesis & anticancer evaluation of new substituted 2-(3,4- Dimethoxyphenyl)benzazoles

Background: The benzazole nucleus is found in many promising small molecules such as anticancer and antibacterial agents. Bendamustine (Alkylating agent), Nocodazole (Mitotic inhibitor), Veliparib (PARP inhibitor), and Glasdegib (SMO inhibitor) are being clinically used as anticancer therapeutic which bear benzimidazole moiety. Based on the principle of bioisosterism, in the present work, 23 compounds belonging to 2-(3,4-dimethoxyphenyl)benzazoles and imidazopyridine series were synthesized and evaluated for their anticancer and antimicrobial activities. Objective: A series of new 2-(3,4-dimethoxyphenyl)-1H-benz(or pyrido)azoles were synthesized and evaluated for their anticancer and antimicrobial activities. Method: N-(5-chloro-2-hdroxyphenyl)-3,4-dimethoxybenzamide 1, was obtained by the amidation of 2-hydroxy-5-chloroaniline with 3,4-dimethoxybenzoic acid by using 1,1'-carbonyldiimidazole. Cyclization of 1 to benzoxazole derivative 2, was achieved by p-toluenesulfonic acid. Other 1H-benz(or pyrido)azoles were prepared by the reaction between 2-aminothiophenol, ophenylenediamine, o-pyridinediamine with sodium metabisulfite adduct of 3,4-dimethoxybenzaldehyde. The NMR assignments of the dimethoxy groups were established by the NOESY spectra. Results: Compound 12, bearing two chlorine atoms at the 5(4) and 7(6) positions of the benzene moiety of benzimidazole was found the most potent analogue against A549 cells with the GI50 value of 1.5 μg/mL. Moreover, 24 showed remarkable cell growth inhibition against MCF-7 and HeLa cells with the GI50 values of 7 and 5.5 μg/mL, respectively. The synthesized compounds have no important antibacterial and antifungal activities. Conclusion: It could be concluded that the introduction of di-chloro atoms at the phenyl ring of 2-(3,4-dimethoxyphenyl)-1H-benzimidazoles increases significant cytotoxicity to selected human tumor cell lines in comparison to other all benzazoles synthesized. Unsubstituted 2-(3,4- dimethoxyphenyl)-imidazopyridines also gave good inhibitory profile against A549 and HeLa cells.

Synthesis and antimicrobial activity of some new 2-phenyl-N-substituted carboxamido-1H-benzimidazole derivatives

Some 1H-benzimidazole-carboxamide derivatives were prepared and their antimicrobial activities against Staphyloccus aureus, Escherichia coli and Candida albicans evaluated. Compounds 18, 22, and 25 exhibited the best activity against Candida albicans.