An expeditious one-pot solvent free synthesis of benzimidazole derivatives

Thakuria, Harjyoti; Das, Gopal

doi:10.3998/ark.5550190.0009.f28

Cited by 35 publications

(4 citation statements)

References 1 publication

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“…292–294°C (Lit. [ 35 ] 293–94°C); FT‐IR (KBr disk) ṽmax: 3550 (O–H), 3070 (Ar–H), 1665 (C=N), 1450–1630 (C=C) cm −1 . 1 H‐NMR (CDCl 3 , 300 MHz, δppm): 12.80 ( s , 1H), 8.16 ( d , J = 2.7 Hz, 2H), 7.67–7.70 ( m , 3H), 7.50–7.53 ( m , 3H), and 7.30–7.33 ( m , 2H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Green synthesis of NiONPs using Trigonella subenervis extract and its applications as a highly efficient electrochemical sensor, catalyst, and antibacterial agent

Mahdavi

Paydarfard

Rezaei‐Seresht

et al. 2021

Applied Organom Chemis

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In recent years, the biosynthesized of metallic nanoparticles has been rapidly growing due to their environmentally synthesis and widespread applications in science and industry. In this study, we have reported the green synthesis of NiONPs using an aqueous extract of Trigonella subenervis (NiONPs@TS). The nanoparticles were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), and energy-dispersive X-ray spectroscopy (EDS). To find various applications for NiONPs@TS, the nanoparticles (NPs) were used as a catalyst for synthesizing some benzimidazole derivatives. The electrochemical behavior and antibacterial activity of NiONPs@TS were also evaluated. FE-SEM images exhibited a uniform spherical morphology in size of 28.21 nm for the biosynthesized nanoparticles. According to the XRD analysis, 26.43 nm was measured for NiONPs@TS crystal size. Benzimidazole derivatives were synthesized using NiONPs@TS as the catalyst with a yield of 69-92%. NiONPs@TS showed a significant electrocatalytic activity to glucose oxidation. The linear response range and detection limit were found to be 10-200 and 3.2 μM, respectively. Furthermore, NiONPs@TS exhibited an acceptable antibacterial activity in various assays, including well diffusion, disk diffusion, minimum inhibition concentration (MIC), and minimum bactericidal concentration (MBC). The best antibacterial activity was obtained against Bacillus subtilis with MIC of 4.0 ± 0.0 μg/ml and MBC of 6.7 ± 2.3 μg/ml. The obtained results showed the ability of NiONPs@TS in different fields such as catalytic, electrochemical sensing, and antibacterial activity, which can be contributed to the presence of biomolecules in T. subenervis extract.

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Section: Methodsmentioning

confidence: 99%

Green synthesis of NiONPs using Trigonella subenervis extract and its applications as a highly efficient electrochemical sensor, catalyst, and antibacterial agent

Mahdavi

Paydarfard

Rezaei‐Seresht

et al. 2021

Applied Organom Chemis

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“…The 1 H -Benzo[ d ]imidazol-2(3 H )-one was effectively synthesized under ultrasonic irradiation in a shorter reaction time of 40 min at 80 °C compared to 6 h under conventional heating [ 50 ] or 22 h stirring [ 51 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, DFT Molecular Geometry and Anticancer Activity of Symmetrical 2,2′-(2-Oxo-1H-benzo[d]imidazole-1,3(2H)-diyl) Diacetate and Its Arylideneacetohydrazide Derivatives

et al. 2022

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To identify new candidate anticancer compounds, we here report the synthesis of benzimidazole derivatives: diethyl 2,2′-(2-oxo-1H-benzo[d]imidazole-1,3(2H)-diyl) diacetate and its arylideneacetohydrazide derivatives, using ultrasonic irradiation and conventional heating. The compounds were confirmed by Nuclear magnetic resonance (NMR) (JEOL, Tokyo, Japan) and Fourier transform infrared spectroscopy (FTIR) spectroscopy (Thermoscientific, Waltham, MA, USA). The molecular structure and electronic properties of the studied compounds were predicted for the acetohydrazide hydrazones. These compounds exist as a mixture of configurational and conformational isomerism as well as amido-amidic acid tautomerism. The NMR spectral data proved the predominance of syn-E amido isomers. In addition, density functional theory (DFT) predicted stability in the gas phase and showed that syn-E amido isomers are the most stable in the presence of an electron donating group, while the anti-isomer is the most stable in the presence of electron-attracting substituents. The anticancer activity of these synthetic compounds 6a, 6b and 6c towards both colon cancer (HCT-116) and cervical cancer (HeLa) cells was examined by MTT assay and DAPI staining. The MTT assay revealed a strong antiproliferative effect against the cancer cells at low concentrations, and interestingly, no significant inhibitory action against the non-cancerous cell line, HEK-293. The IC50 values for HCT-116 were 29.5 + 4.53 µM, 57.9 + 7.01 µM and 40.6 + 5.42 µM for 6a, 6b, and 6c, respectively. The IC50 values for HeLa cells were 57.1 + 6.7 µM, 65.6 + 6.63 µM and 33.8 + 3.54 µM for 6a, 6b, and 6c, respectively. DAPI staining revealed that these synthesized benzimidazole derivatives caused apoptotic cell death in both the colon and cervical cancer cells. Thus, these synthetic compounds demonstrate encouraging anticancer activity as well as being safe for normal human cells, making them attractive candidates as anticancer agents.

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“…Also, a totally solvent-free and a deep eutectic solvent synthesis of the abovesaid compounds has been reported, but the use of high temperatures, toxic compounds such as urea, and so forth in these reactions is undesirable. [28,34] Although small amounts of catalyst allow the reaction to take place under mild conditions and at lower temperatures. In fact, using a catalyst is a way to save energy.…”

Section: Introductionmentioning

confidence: 99%

New phosphonium bromobismuthate as selective catalytic reagent in the heterocyclization reactions

Salmasi

Gholizadeh

Salimi

et al. 2023

Applied Organom Chemis

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A new hybrid phosphonium bromobismuthate compound was synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT‐IR, differential scanning calorimetry (DSC) and single‐crystal X‐ray diffraction analysis. The crystal packing structures of title compound were stabilized by various intermolecular interactions especially of the type CH···Br hydrogen bonds between phosphonium cations and [Bi2Br9]3− anion. The relative contribution of various close contacts and 2D fingerprint plots of title compound and three analogous structures obtained from Cambridge Structural Database (CSD) were investigated by Hirshfeld surface analysis. Furthermore, the catalytic activity of title compound was investigated in heterocyclization reaction for the synthesis of significant and pharmacologically useful benzimidazole and benzoxazole derivatives. The results indicated that the yields of the product for aldehydes bearing p‐substituents and o‐substituents were higher than for m‐substituent ones. In addition to selectivity, simplicity of operation, waste minimization, ease of manipulation, short reaction time, excellent yield of product, and easy workup, this technique uses title compound as the catalyst, which is green, recyclable, soft, remarkably nontoxic, and easy to handle.

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An expeditious one-pot solvent free synthesis of benzimidazole derivatives

Abstract: A one-pot efficient synthesis of biologically active benzimidazole derivatives has been achieved under solvent-free green conditions, with unsurpassed atom economy, by a simple grinding method followed by heating.

Cited by 35 publications

References 1 publication

Green synthesis of NiONPs using Trigonella subenervis extract and its applications as a highly efficient electrochemical sensor, catalyst, and antibacterial agent

Green synthesis of NiONPs using Trigonella subenervis extract and its applications as a highly efficient electrochemical sensor, catalyst, and antibacterial agent

Synthesis, DFT Molecular Geometry and Anticancer Activity of Symmetrical 2,2′-(2-Oxo-1H-benzo[d]imidazole-1,3(2H)-diyl) Diacetate and Its Arylideneacetohydrazide Derivatives

New phosphonium bromobismuthate as selective catalytic reagent in the heterocyclization reactions

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