2208-58-4Relevant academic research and scientific papers
Exploring beta amyloid cleavage enzyme-1 inhibition and neuroprotective role of benzimidazole analogues as anti-alzheimer agents
Gurjar, Archana S.,Solanki, Vivek S.,Meshram, Ankita R.,Vishwakarma, Suchita S.
, p. 864 - 873 (2020)
Beta amyloid cleavage enzyme-1 (BACE1) is the key enzyme involved in Aβ peptide formation in Alzheimer's disease pathogenesis. We intend to target this enzyme by exploring benzimidazole analogues against BACE1 as potential anti-Alzheimer agents. Docking studies were performed to determine the hydrogen bond interactions between the designed molecules and the target protein's active site. Research indicates the relationship between oxidative stress and Aβ effect in precipitating neurodegeneration; hence, the series was also studied in vitro to ascertain its neuroprotective role by performing the lipid peroxidation assay. In silico absorption, distribution, metabolism, and excretion studies were undertaken to assess the drug-like suitability of the analogues. To judge the effect of the synthesized analogues on central nervous system (CNS), toxicity and memory model studies were conducted on mice. Thus, overall results showcase analogues 11 and 14 as the most promising ones with the dual role of BACE1 inhibition and neuroprotection, along with memory retention.
Green synthesis of benzimidazole derivatives under ultrasound irradiation using Cu-Schiff base complexes embedded over MCM-41 as efficient and reusable catalysts
Bharathi, M.,Indira, S.,Induja, E.,Mahalakshmi, T.,Shamuga Bharathi, K.,Vinoth, G.
, (2019)
We have synthesized two recoverable catalysts by covalently attaching complexes such as Cu-complex-phen and Cu-complex-bipy on MCM-41 through a greener synthetic route. FT-IR, EDX, SEM and TEM microscopy, XRD analysis, N2 adsorption and desorpt
Reevaluating the synthesis of 2,5-disubstituted-1H-benzimidazole derivatives by different green activation techniques and their biological activity as antifungal and antimicrobial inhibitor
Penieres-Carrillo, José-Guillermo,Ríos-Guerra, Hulme,Pérez-Flores, Javier,Rodríguez-Molina, Braulio,Torres-Reyes, ángeles,Barrera-Téllez, Francisco,González-Carrillo, Jessica,Moreno-González, Lessly,Martínez-Zaldívar, Alejandro,Nolasco-Fidencio, Juan-Jesús,Matus-Meza, Audifás-Salvador,Luna-Mora, Ricardo-Alfredo
, p. 436 - 455 (2020)
A comparative study concerned with the preparation of diversely substituted-1H-benzimidazole under different green activation techniques and conventional methods is reported. Data are collected for infrared, ultrasound, microwave, and simultaneous irradiation with US and IR sources, as this last strategy shows an important improvement. Further, the small library of potentially bioactive benzimidazole 17-76 synthesized was screened as an antifungal and antimicrobial agent. Strong activity against Candida albicans and Staphylococcus aureus was observed. Remarkably, 2-(4-aminophenyl)-5-phenylamino-1H-benzimidazole 63 resulted better than that of reference drugs miconazole with a zone of inhibition up to 42 mm. Likewise, 2-(2-aminophenyl)-1H-benzimidazole 21 showed substantial antimicrobial activity against MRSA strain. When assayed by the microdilution method, this azaheterocyclic compound presented a minimum inhibitory concentration (MIC) ≥ 16.4 μg/100 mL and a bacterial percentage reduction of 96%.
Facile and selective synthesis of 2-substituted benzimidazoles catalyzed by FeCl3/Al2O3
Chen, Guo-Feng,Dong, Xiao-Yun
, p. 289 - 293 (2012)
2-Substituted benzimidazoles were synthesized in a single pot from aromatic aldehydes and o-phenylenediamine catalyzed by FeCl3/Al 2O3 in DMF at ambient temperature attained good yields and high selectivity.
Single Heteroatom Fine-Tuning of the Emissive Properties in Organoboron Complexes with 7-(Azaheteroaryl)indole Systems
Más-Montoya, Miriam,Usea, Laura,Espinosa Ferao, Arturo,Montenegro, María F.,Ramírez De Arellano, Carmen,Tárraga, Alberto,Rodríguez-López, José N.,Curiel, David
, p. 3296 - 3302 (2016)
The application of organoboron compounds as light-absorbing or light-emitting species in areas as relevant as organic electronics or biomedicine has motivated the search for new materials which contribute to the progress of those applications. This articl
[Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)]: Synthesis, crystal structure, catalytic activity and DFT study
Brahman, Dhiraj,Chhetri, Sailesh,Kamath, Amarjit,McArdle, Patrick,Sinha, Biswajit
, (2021/09/04)
Metal-organic hybrid complexes often exhibit large surface area, pore volume, fascinating structures and potential applications including catalytic applications. Hence a new metal-organic hybrid complex [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)] was synthesized using conventional method. Physico-chemical characterization of the complex was performed with FTIR spectroscopy, single crystal X-ray diffraction, TGA, EPR and FESEM. Single crystal X-ray diffraction study suggests it to be three dimensional with space group P212121 (orthorhombic). The crystal achieves its three-dimensional structure and stability through extensive intermolecular hydrogen bonding. Hirshfeld surface analysis, catalytic activity and DFT study of the complex was also performed. The synthesized complex acts as good catalyst in benzimidazole synthesis with good recyclability as catalyst up to 5th run.
1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles
Kalhor, Mehdi,Zarnegar, Zohre
, p. 519 - 540 (2021/12/03)
In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]
UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W-ZnO@NH2nanoparticles
Chen, Ruijuan,Jalili, Zahra,Tayebee, Reza
, p. 16359 - 16375 (2021/05/19)
Heterogeneous photocatalysts proffer a promising method to actualize eco-friendly and green organic transformations. Herein, a new photochemical-based methodology is disclosed in the preparation of a wide range of benzimidazoles through condensation of o-phenylenediamine with benzyl alcohols in the air under the illumination of an HP mercury lamp in the absence of any oxidizing species catalyzed by a new photocatalyst W-ZnO@NH2-CBB. In this photocatalyst, coomassie brilliant blue (CBB) is heterogenized onto W-ZnO@NH2 to improve the surface characteristics at the molecular level and enhance the photocatalytic activity of both W-ZnO@NH2 and CBB fragments. This unprecedented heterogeneous nanocatalyst is also identified by means of XRD, FT-IR, EDS, TGA-DTG, and SEM. The impact of some influencing parameters on the synthesis route and effects on the catalytic efficacy of W-ZnO@NH2-CBB are also assessed. The appropriate products are attained for both the electron-withdrawing and electron-donating substituents in the utilized aromatic alcohols. Furthermore, preparation of benzimidazoles is demonstrated to occur mainly via a radical mechanism, which shows that reactive species such as ·O2-, OH and h+ would be involved in the photocatalytic process. Stability and reusability studies also warrant good reproducibility of the nanophotocatalyst for at least five runs. Eventually, a hot filtration test proved that the nanohybrid photocatalyst is stable in the reaction medium. Using an inexpensive catalyst, UV-vis light energy and air, as a low cost and plentiful oxidant, puts this methodology in the green chemistry domain and energy-saving organic synthesis strategies. Finally, the anticancer activity of W-ZnO nanoparticles is investigated on MCF7 breast cancer cells by MTT assay. This experiment reveals that the mentioned nanoparticles have significant cytotoxicity towards the selected cell line.
Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols
Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali
, p. 1049 - 1067 (2020/09/11)
An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized by FT-IR, XRD, FE-SEM, TEM, VSM, TGA, EDX, DLS, and ICP analyses. The optimum range of parameters such as time, temperature, amount of catalyst, and solvent were investigated for the domino one-pot benzimidazole and Biginelli reactions to find the optimum reaction conditions. The catalyst was compatible with a variety of benzyl alcohols, which provides favorable products with good to high yields for all of derivatives. Hot filtration and Hg poisoning tests from the nanocatalyst revealed the stability, low metal leaching and heterogeneous nature of the catalyst. To prove the synergistic and cooperative effect of the catalytic system, the various homologues of the catalyst were prepared and then applied to a model reaction separately. Finally, the catalyst could be filtered from the reaction mixture simply, and reused for five consecutive cycles with a minimum loss in catalytic activity and performance. Graphic Abstract: A new magnetically recyclable Cu/Mn bimetallic catalyst has been developed for domino one-pot oxidation-condensation of benzimidazole and Biginelli reactions from alcohols. [Figure not available: see fulltext.]
Application of sulfonic acid fabricated cobalt ferrite nanoparticles as effective magnetic nanocatalyst for green and facile synthesis of benzimidazoles
Yadav, Priyanka,Kakati, Praachi,Singh, Preeti,Awasthi, Satish K.
, (2021/02/06)
This work represents the design and synthesis of efficient sulfonated cobalt ferrite solid acid catalyst. The synthesized solid acid green catalyst was characterized using various techniques viz. FT-IR, powder XRD, SEM, TEM and VSM. The obtained catalyst was used to synthesize biologically significant 2-substituted benzimidazole derivatives by condensation between o-phenylenediamine with various aromatic, aliphatic and heterocyclic aldehydes. High yield (up to 98 %), short reaction time (10?25 min), mild reaction condition, wide functional group tolerance, easy work-up procedure and excellent values of green chemistry metrices such as lower E factor (0.126), high RME value (88.83 %), carbon efficiency (100 %) and high atom economy (AE) value (90.65 %), are some salient features of the present catalytic system. Moreover, the catalyst recovery by simply using an external magnet and catalyst reusability up to 7 times without any significant loss in catalytic efficiency are some additional remarkable features of the current protocol.
