30458-48-1

Usage

Structure

A derivative of benzimidazole with a methoxy group at the 5th position and a 4-methoxyphenyl group at the 2nd position of the benzimidazole ring.

Usage

Commonly used as a building block in organic synthesis, particularly in the pharmaceutical industry for the production of various drugs and biologically active molecules.

Importance

Its specific chemical properties and potential biological activities make it a valuable tool for medicinal chemistry research and drug development.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 96-96-8 4-methoxy-2-nitroaniline 
• 16133-49-6 5-methoxy-2-nitroaniline 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 54998-29-7 ethyl 4-methoxybenzimidate hydrochloride 
• 15965-54-5 2-chloro-5-methoxy-1H-1,3-benzimidazole 
• 71195-76-1 hydroxy-(4-methoxy-phenyl)-methanesulfonic acid ; anisaldehyde sulfite sodium 

Relevant academic research and scientific papers

Dehalogenation reaction photocatalyzed by homoleptic copper(i) complexes associated with strongly reductive sacrificial donors

In order to perform challenging reduction reactions with light, at low cost and low toxicity, we aim at using for the first time a reductive quenching cycle with a simple, strongly colored homoleptic copper(i) complex [Cu(dipp)2]+(dipp = 2,9-diisopropyl-1,10-phenanthroline). Complexes of this family being weak photo-oxidants, we specifically designed and synthesized powerful, recyclable sacrificial electron donors D. We demonstrate that, during irradiation with LED light in the presence of D, the strong reductant [Cu(dipp)2]0is efficiently photo-generated. Further, we present the first photochemical reaction using photo-generated [Cu(dipp)2]0and evidence that the kinetics of the overall reaction are strongly affected by the oxidation potential of the sacrificial donorE(D+/D). Adapting the thermodynamics of sacrificial donors D and [Cu(dipp)2]+has thus allowed us to unlock a brand new concept, giving access to cheap, non-toxic solar light-generated very strong reductive power.

Synthesis, bioevaluation and docking studies of some 2-phenyl-1H-benzimidazole derivatives as anthelminthic agents against the nematode Teladorsagia circumcincta

Gastrointestinal nematode infections are the main diseases in herds of small ruminants. Resistance to the main established drugs has become a worldwide problem. The purpose of this study is to obtain and evaluate the in vitro ovicidal and larvicidal activity of some 2-phenylbenzimidazole derivatives on susceptible and resistant strains of Teladorsagia circumcincta. Compounds were prepared by known procedures from substituted o-phenylenediamines and arylaldehydes or intermediate sodium 1-hydroxyphenylmethanesulfonate derivatives. Egg Hatch Test (EHT), Larval Mortality Test (LMT) and Larval Migration Inhibition Test (LMIT) were used in the initial screening of compounds at 50 μM concentration, and EC50 values were determined for the most potent compounds. Cytotoxicity evaluation of compounds was conducted on human Caco-2 and HepG2 cell lines to calculate their Selectivity Indexes (SI). At 50 μM concentration, nine out of twenty-four compounds displayed more than 98% ovicidal activity on a susceptible strain, and four of them showed more than 86% on one resistant strain. The most potent ovicidal benzimidazole (BZ) 3 showed EC50 = 6.30 μM, for the susceptible strain, while BZ 2 showed the lowest EC50 value of 14.5 μM for the resistant strain. Docking studies of most potent compounds in a modelled Teladorsagia tubulin indicated an inverted orientation for BZ 1 in the colchicine binding site, probably due to its fair interaction with glutamic acid at codon 198, which could justify its inactivity against the resistant strain of T. circumcincta.

Sulfur/DABCO Promoted Reductive Coupling/Annulation Cascade Reaction between o -Hydroxy/Amino Nitrobenzenes and Benzaldehydes

Sulfur/DABCO was found to be an efficient reagent in promoting- the reductive coupling/annulation of o -nitrophenols or o -nitroanilines with benzaldehydes. This method represents a simple, straightforward, and green approach to the construction of benz-oxazoles and benzimidazoles.

Eco-friendly highly efficient solvent free synthesis of benzimidazole derivatives over sulfonic acid functionalized graphene oxide in ambient condition

Abstract: Sulfonated graphene oxide (GO-HSO3) heterogeneous catalyst was prepared at molecular level and characterized by using various modern analytic and spectroscopic methods. Using prepared heterogeneous catalyst GO-HSO3, benzimidazole synthesis was carried out by means of reacting diamine and aldehyde at room temperature in solvent free condition. The catalyst GO-HSO3 showed tremendous catalytic activity in selective synthesis of benzimidazole, as a result 100?% conversion of reactants and up to 89.0?% yield of respective benzimidazole was achieved using 0.1?mg of catalyst in very short reaction duration. The GO-HSO3 catalyst was separated from the reaction mixture by simple filtration process at the end of reaction and reused for six successive cycles without noteworthy loss of catalytic activity and selectivity. Key advantageous of this protocol is high yield, low cost, and easy work-up procedure as well as short reaction time and solvent free condition. The present method is found eco-friendly, highly efficient, solvent free, high yielding, and clean method for the synthesis benzimidazole derivatives at room temperature. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives

A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO) scavenging, superoxide radical anion (O2 -) scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO scavenging activity (EC50 = 46 μM) in vitro had a significant reduction of 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations.

2-Phenyl-1-[4-(2-piperidine-1-yl-ethoxy)benzyl]-1H-benzimidazoles as ligands for the estrogen receptor: Synthesis and pharmacological evaluation

2-Phenyl-1H-benzimidazoles 7a-e were synthesized and tested for gene activation on ERα-positive MCF-7 breast cancer cells, stably transfected with the reporter plasmid EREwtcluc (MCF-7-2a cells). None of the compounds showed agonistic properties, but they antagonized dependent on hydroxyl groups at the benzimidazole core (5- or 6-OH) and at the aromatic ring in the 2-position (4-OH) in high concentrations the gene activation induced by estradiol (E2, 1 nM). All compounds exhibited significant antiproliferative properties on MCF-7 cells but they were inactive against hormone independent, ER negative MDA-MB-231 cells.

Synthesis of 2-arylbenzimidazoles via microwave Suzuki-Miyaura reaction of unprotected 2-chlorobenzimidazoles

A series of 2-arylbenzimidazoles were synthesized via microwave-mediated Suzuki-Miyaura coupling of 2-chloro benzimidazoles and either arylboronic acids or aryltrifluoroborate salts. The most notable aspect of the present work is that there is no need for

Synthesis and antimicrobial activity of 1-dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives

1-(Dialkylaminomethyl)-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives 1 have been synthesized by reacting 2-phenylbenzimidazole derivatives with formaldehyde and a secondary amine. The derivatives of 2-phenylbenzimidazole were obtained by reacting the bisulfide addition product of substituted benzaldehydes with 4-substituted-o-phenylenediamines. Their structures were confirmed by microanalysis, IB and NMB spectral analysis. Antimicrobial activity of the compounds was investigated by the microdilution susceptibility test in Mueller-Hinton Broth and Sabouraud Dextrose Broth was used for the determination of antibacterial and antifungal activities. Test organisms: Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as Gram-positive bacteria, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853 as Gram-negative bacteria, and Candida albicans, C. parapsilosis, C. stellatoidea as yeast-like fungi. Compounds 1a, 1b, 1c, 1e and 1i showed slight to moderate activity against all microorganisms. Compound 1g showed the highest activity. It was found more potent than streptomycin against Enterococcus faecalis and Pseudomonas aeruginosa.

Studies on analgesic and anti-inflammatory activities of 1- dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives

In this study the analgesic and anti-inflammatory activity of 1,2,5- trisubstituted benzimidazole derivatives have been examined. Analgesic activities of these compounds were investigated by using the modified Koster test. Among the compounds synthesized especially compound 1g (1- diethylaminomethyl)-2-(p-chlorophenyl)-5-nitro benzimidazole hydrochloride) has shown higher activity than acetylsalicylic acid (ASA) and indometacin. Compound 1e (1-(diethylaminomethyl)-2-(p-methoxyphenyl)-5-nitro benzimidazole hydrochloride, 1f (1-(diethylaminomethyl)-2-(p-tolyl)-5-nitro henzimidazole hydrochloride and 1i (1-(pipenridinomethyl)-2-(p-methoxyphenyl)-5-nitro benzimidazole hydrochloride) proved as potent as the standard ASA. Therefore the compounds 1e, 1f, 1g and 1i were screened for their anti-inflammatory activities using the carrageenan-induced hind paw edema test. Except 1g all compounds were almost inactive against this model of inflammation compared to indometacin.