174422-10-7

Basic information

• Product Name: 2-FURAN-2-YL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID
• Synonyms: 2-FURAN-2-YL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID;2-Furan-2-yl-3H-benzoimidazole-5-carboxylic;2-(Furan-2-yl)-1H-benzo[d]iMidazole-6-carboxylic acid;2-(furan-2-yl)-1H-1,3-benzodiazole-6-carboxylic acid
• CAS NO: 174422-10-7
• Molecular Formula: C12H8N2O3
• Molecular Weight: 228.2
• Mol File: 174422-10-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 522.8°Cat760mmHg
• Flash Point: 270°C
• Appearance: /
• Density: 1.465g/cm³
• Vapor Pressure: 9.3E-12mmHg at 25°C
• Refractive Index: 1.703
• CAS DataBase Reference: 2-FURAN-2-YL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FURAN-2-YL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(174422-10-7)
• EPA Substance Registry System: 2-FURAN-2-YL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID(174422-10-7)

Safety Data

• Hazardous Substances Data: 174422-10-7(Hazardous Substances Data)

Usage

General Description

2-Furan-2-yl-3H-benzoimidazole-5-carboxylic acid is a chemical compound with potential therapeutic applications. It belongs to the class of benzimidazole derivatives and contains a furan ring and a carboxylic acid group. 2-FURAN-2-YL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID has been studied for its pharmacological properties, including its potential as an anti-inflammatory and anti-cancer agent. Its unique structure allows for potential interactions with various biological targets, making it a promising candidate for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C12H8N2O3/c15-12(16)7-3-4-8-9(6-7)14-11(13-8)10-2-1-5-17-10/h1-6H,(H,13,14)(H,15,16)

Upstream product

• 98-01-1 furfural 
• 619-05-6 3,4-diaminobenzoic acid 

Relevant articles and documents

Inhibition of aflatoxin B1 biosynthesis and down regulation of aflR and aflB genes in presence of benzimidazole derivatives without impairing the growth of Aspergillus flavus

Aflatoxins are mutagenic secondary metabolites produced by certain ubiquitous saprophytic fungi. These contaminate agricultural crops and pose a serious health threat to humans and livestock all over the world. Benzimidazole and its derivatives are biologically active heterocyclic compounds known for their fungicidal activity. In the present study, second and sixth position substituted benzimidazole derivatives are tested for their antifungal and anti-aflatoxigenic activity. Aflatoxigenic strain of Aspergillus flavus cultured in Yeast extract sucrose (YES) medium as well as in rice in the presence and absence of test compounds. 2-(2-Furyl) benzimidazole (FBD) showed complete inhibition of fungal growth at 50 μg/mL. However, the polar derivatives of FBD viz. 6-NFBD, 6-AFBD, 6-CAFBD, and 6-CFBD did not impair the fungal growth but effectively inhibited aflatoxin B1 biosynthesis. Significant down-regulation of aflR gene involved in regulation and aflB structural gene for aflatoxin B1 biosynthesis was observed in presence of 6-NFBD. These benzimidazole derivatives also showed good anti-aflatoxigenic activity in rice, though the IC50 concentrations in rice were comparatively higher than those in YES medium. This study summarizes the most notable structure-activity relationship (SAR) of 2-(2-Furyl) benzimidazoles for anti-aflatoxigenic and anti-fungal activities. These molecules can be further studied for their applications in industrial fermentation processes vulnerable to mold growth and subsequent aflatoxin B1 synthesis like koji fermentation, cheese production, etc.

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.