27146-12-9

Usage

Purity

95%

Molecular Weight

178.16 g/mol

Appearance

Pale yellow solid

Solubility

Slightly soluble in water, soluble in common organic solvents

Melting Point

240-245°C

Boiling Point

Not applicable, as it is a solid

Functional Groups

Nitro group, furyl substituent, benzimidazole core

Synthesis

Derived from benzimidazole through chemical reactions involving the addition of a nitro group and a furyl substituent

Uses

Utilized in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals

Pharmacological and Biological Activities

Known for its potential pharmacological and biological activities

Safety

Handle with care and follow proper safety protocols due to potential health and environmental hazards.

Upstream product

• 98-01-1 furfural 
• 99-56-9 4-Nitrophenylene-1,2-diamine 

Downstream Products

• 37128-74-8 2-(furan-2-yl)-1H-1,3-benzodiazol-5-amine 
• 56119-96-1 2-furan-2-yl-7-methyl-1(3),6-dihydro-imidazo[4,5-f]quinolin-9-one 

Relevant academic research and scientific papers

Synthesis and Reactivity of Fusion Product of 2-Methylthiazole Fragment to 2-(Furan-2-yl)benzimidazole

Reaction of 1,2-diamino-4-nitrobenzene with furan-2-carbaldehyde in the presence of copper sulfate afforded 2-(furan-2-yl)-5(6)-nitro-1H-benzimidazole. Its N-methylation provided 1-methyl-5(6)-nitro isomers. After reduction of isomers with tin in conc. HCl a pure 3-methyl-2-(furan-2-yl)benzimidazol-5-amine was obtained. The condensation of this amine with acetic anhydride led to the formation of N-[3-methyl-2-(furan-2-yl)benzimidazol-5-yl]acetamide whose treatment with excess P2S5 in anhydrous pyridine resulted in the corresponding thioamide. The latter was oxidized with K3[Fe(CN)6] in alkaline environment to obtain 2,8-dimethyl-7-(furan-2-yl)-8H-imidazo[4,5-g][1,3]benzothiazole. Its reactions of electrophilic substitution were studied: nitration, bromination, sulfonation, formylation, acylation. The substituent is introduced exclusively in the position 5 of the furan ring.

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.

COMPOSITION FOR INHIBITING SYNTHESIS OF MYCOTOXIN WITHOUT AFFECTING THE GROWTH OF THE FUNGI

A composition for inhibiting the growth of mycotoxins without affecting the growth of fungi is provided. The mycotoxin is an Aflatoxin and the fungus is an Aspergillus. The anti-aflatoxin composition comprises benzimidazole derivatives of Formula, where the A is hydrogen or C1-C6 alkyl or C6-C14 aryl; B is C1-C10 alkyl or C6-C14 aryl or oxygen, sulfur, nitrogen containing heteroaryl; C and D are hydrogen or C1-C6 alkyl or C1-C6 alkoxyl or C6-C14 aryl; E is hydrogen or nitro or cyano or carboxyl or acetamidoxime or amidoxime or C1-C6 alkyl or C1-C6 alkoxyl or C6-C14 aryl or oxygen, sulfur, and nitrogen containing heteroaryl; F is hydrogen or C1-C6 alkyl or C1-C6 alkoxyl or C6-C14 aryl or oxygen, sulfur, and nitrogen containing heteroaryl, and mixture thereof with corresponding salts.

SUBSTITUTED IMIDAZO[1,5-A]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazo[1,5-a]pyrimidines and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,5-a]pyrimidine compounds described herein include substituted 2,4-dimethyl-N-phenylimidazo[1,5-a]pyrimidine-8-carboxamide compounds and variants thereof.

SUBSTITUTED PYRAZOLO(1,5-A)PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted pyrazolo[l,5-a]pyrimidine and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted pyrazolo[l,5-a]pyrimidine compounds described herein include 5,7- dimethyl-N-phenylpyrazolo[l,5-a]pyrimidine-3-carboxamide compounds and variants thereof.

Construction and screening of 2-aryl benzimidazole library identifies a new antifouling and antifungal agent

Biofouling is the undesirable growth of organisms on artificial and natural structures immersed in either seawater or freshwater. It causes huge economic loss and also the global prohibition on known antifouling agents has led to an increased search for safe and effective antifouling agents. In the past, marine natural products have shown tremendous potential by providing new skeletons that could be used as eco-friendly antifouling agents. The library of the 2-aryl benzimidazole core inspired from marine natural products (oroidin and bromoageliferin) was identified and synthesized to explore the antifouling/antifungal properties for the first time. Twelve 2-aryl benzimidazole derivatives were synthesized and evaluated for their antifouling performance against 10 strains of marine biofilm forming bacteria developed on copper panels exposed for 14 days at Dona Paula, Arabian Sea, India. These compounds were also evaluated for their antibacterial and antifungal activities. Two compounds, i.e.4j and 4l, showed a broad spectrum of antifouling activities against nine marine fouling species, whereas 2-(furan-2-yl)-1H-benzo[d] imidazole 4g showed strong antifungal activity against the clinical pathogen Aspergillus niger. Our results reveal that the 2-aryl substituent on the benzimidazole core had strong impact on their biological profile. Moreover, here we report the first study of the benzimidazole library as a target in 10 representative fouling strains.

DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media

An efficient synthetic method has been developed for the facile synthesis of 2-substituted benzimidazoles in organized aqueous media in the presence of a surfactant (viz. DBSA) as catalyst and I2 as co-catalyst. The method described has the advantages of operational simplicity, excellent yields, high chemoselectivity, and clean and green reaction profile.

Imidazo(4,5-f)quinolines useful as immunomodulating agents

The present invention involves compounds of the class of imidazo[4,5-f]quinolines and methods for enhancing the immune response system of mammals which comprises systemically administering to mammals having a depressed immune function an effective but non