Trimethylsilyl Chloride Catalyzed Synthesis of Substituted Benzimidazoles Using Two Phase System Under Microwave Conditions, and Their Antimicrobial Studies

Karuvalam, Ranjith P.; Haridas, Karickal R.; Shetty, Suchetha. N

doi:10.4067/s0717-97072012000200014

Cited by 11 publications

(3 citation statements)

References 6 publications

(7 reference statements)

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“…1 5-Nitrobenzimidazole (2a). 44 4-Nitro-1,2-phenylendiamine (1.784 g, 11.65 mmol) and 40 mL of formic acid were added to a 100 mL flask and refluxed at 110 °C for 4 h, giving a green solution. The mixture was cooled to 0 °C, and the product was precipitated by neutralization with concentrated ammonia.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Rhodium(I) N-Heterocyclic Carbene Bioorganometallics as in Vitro Antiproliferative Agents with Distinct Effects on Cellular Signaling

et al. 2015

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Organometallics with N-heterocyclic carbene (NHC) ligands have triggered major interest in inorganic medicinal chemistry. Complexes of the type Rh(I)(NHC)(COD)X (where X is Cl or I, COD is cyclooctadiene, and NHC is a dimethylbenzimidazolylidene) represent a promising type of new metallodrugs that have been explored by advanced biomedical methods only recently. In this work, we have synthesized and characterized several complexes of this type. As observed by mass spectrometry, these complexes remained stable over at least 3 h in aqueous solution, after which hydrolysis of the halido ligands occurred and release of the NHC ligand was evident. Effects against mitochondria and general cell tumor metabolism were noted at higher concentrations, whereas phosphorylation of HSP27, p38, ERK1/2, FAK, and p70S6K was induced substantially already at lower exposure levels. Regarding the antiproliferative activity in tumor cells, a clear preference for iodido over chlorido secondary ligands was noted, as well as effects of the substituents of the NHC ligand.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Rhodium(I) N-Heterocyclic Carbene Bioorganometallics as in Vitro Antiproliferative Agents with Distinct Effects on Cellular Signaling

et al. 2015

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“…This confirms the hypothesis that there is a direct relationship between the antifungal activity and the electron withdrawing effect of substituents. Compound 5 (5-Br) was active against the selected strains with MIC equivalent to half that exhibited by amphotericin B [31].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents

et al. 2015

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A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1H-benzo 15207 activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

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“…[38][39] However, Microwave-assisted organic synthesis (MAOS) continues to affect synthetic chemistry significantly by enabling rapid, reproducible experiments. [40][41][42][43] Particularly, the use of milder reagents has improved both the yield and purity of this reaction. [44][45] Today, cancer patients are being treated with radiotherapy, chemotherapy and surgical interventions.…”

Section: Introduction *mentioning

confidence: 99%

Benzimidazole Schiff bases microwave assisted synthesis and the effect on leukemia cells with flow cytometry

CELIK¹,

Vatansev²,

Koç³

2019

Rev.Roum.Chim.

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The present paper introduces a simple and efficient method for the synthesis of a 2-aryl-substituted benzimidazole by heterocyclization of 1,2phenylenediamine and 5-aminoisophthalic acid in the presence of polyphosphoric acid as catalyst under solvent-less conditions, which produced good yield of corresponding benzimidazoles in a short reaction time. Two new bisbenzimidazoles and tetrakisbenzimidazole Schiff bases were synthesized by reaction between 3,5-di(1H-benzo[d]imidazol-2-yl)aniline (BIMA) and terephthalaldehyde or 4-formylbenzoic acid. The condensations proceed in short time to give products which, in certain instances, are not readily attainable by conventional condensation techniques. Due to its good performance, the microwave device used in household was preferred. The structures of the compounds were assigned by FT-IR, 1 H NMR, 13 C NMR and elemental analysis. The effects of benzimidazoles and Schiff bases on the cancerous cells have been known. Synthesized by bisbenzimidazole and bisbenzimidazole/tetrakisbenzimidazole-Schiff bases derivatives 3,5-di(1Hbenzo[d]imidazol-2-yl)aniline (BIMA), N,N'-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(3,5-di(1H-benzo[d]imidazol-2-yl)aniline) (PM-BIMA), (E)-4-((3,5-di(1H-benzo[d]imidazol-2-yl)phenylimino)methyl)benzoic acid (BIM-PMBA) with flow cytometric analysis was performed, blastic cells containing 90%. We measured rates of cell death in cells blast on the matter. leukaemia cells

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Trimethylsilyl Chloride Catalyzed Synthesis of Substituted Benzimidazoles Using Two Phase System Under Microwave Conditions, and Their Antimicrobial Studies

Cited by 11 publications

References 6 publications

Rhodium(I) N-Heterocyclic Carbene Bioorganometallics as in Vitro Antiproliferative Agents with Distinct Effects on Cellular Signaling

Rhodium(I) N-Heterocyclic Carbene Bioorganometallics as in Vitro Antiproliferative Agents with Distinct Effects on Cellular Signaling

Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents

Benzimidazole Schiff bases microwave assisted synthesis and the effect on leukemia cells with flow cytometry

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