190780-24-6Relevant articles and documents
Synthesis, crystal structure, and characterization of new 2,4,5-triphenyl imidazole: 4,5-diphenyl-2-(3,4,5-trimethoxyphenyl)-1 h-imidazole
Viveka,Prabhuswamy,Dinesha,Lokanath,Nagaraja
, p. 83 - 94 (2014)
The substituted triarylimidazole, C24H22N2O3, was prepared from the three-component one-pot condensation reaction and the product was crystallized by using dimethylformamide. The structure of the compound was confirmed by elemental analysis, FT-IR, thermogravimetric analysis (TGA), UV-Visible and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic crystal system in the space group P21 /c with unit cell parameters a = 10.509(3) A, b = 18.748(5) A, c = 22.016(6) A, β = 90.844(5)°, and Z = 8. The crystal structure of the compound was stabilized by the inter-molecular interactions of types N-HsssN, C-HsssO, and C-HsssN, and intra-molecular interactions of the type C-HsssO. The structure also involves C-Hsssπ interactions.
An eco-friendly, one pot synthesis of tri-substituted imidazoles in aqueous medium catalyzed by RGO supported Au nano-catalyst and computational studies
Biswas, Sudip,Das, Madhurima,Ghatak, Avishek,Sinha, Debopam
, (2021/07/09)
An eco-compatible, mild and operationally simple aqueous phase protocol for the synthesis of 2,4,5-trisubstituted imidazoles has been achieved with high substrate scope using supported Au nanoparticles. The catalyst can be recovered for the subsequent rea
Pumice-modified cellulose fiber: An environmentally benign solid state hybrid catalytic system for the synthesis of 2,4,5-triarylimidazole derivatives
Gharibi, Saideh,Maleki, Ali,Taheri-Ledari, Reza,Valadi, Kobra
, (2020/03/13)
In this study, we developed an instrumental hybrid catalytic system comprising cellulose fiber and volcanic pumice powder, which was applied as a suitable organic–inorganic hybrid catalyst for the synthesis of 2,4,5-triarylimidazole derivatives. High reaction yields (97%) were obtained in short reaction times (20 min) using this catalytic system. In physical terms, the high porosity of pumice provides an extremely high active surface area for electronic interactions among the components. Moreover, the most distinctive properties of this catalytic system are high biodegradability, simple separation of the catalyst, and good reusability. The natural pumice can be recovered easily using an external magnet and reused with no significant decline in the catalytic activity. The structural characteristics of this efficient catalytic system were assessed using various analytical methods.
Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
Higuera, Natalia López,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
supporting information, p. 225 - 229 (2019/01/14)
The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.
In silico studies, synthesis and pharmacological evaluation to explore multi-targeted approach for imidazole analogues as potential cholinesterase inhibitors with neuroprotective role for Alzheimer's disease
Gurjar, Archana S.,Darekar, Mrunali N.,Yeong, Keng Yoon,Ooi, Luyi
, p. 1511 - 1522 (2018/02/13)
Alzheimer's disease (AD) is a progressive neurodegenerative disorder with multiple factors associated with its pathogenesis. Our strategy against AD involves design of multi-targeted 2-substituted-4,5-diphenyl-1H-imidazole analogues which can interact and inhibit AChE, thereby, increasing the synaptic availability of ACh, inhibit BuChE, relieve induced oxidative stress and confer a neuroprotective role. Molecular docking was employed to study interactions within the AChE active site. In silico ADME study was performed to estimate pharmacokinetic parameters. Based on computational studies, some analogues were synthesized and subjected to pharmacological evaluation involving antioxidant activity, toxicity and memory model studies in animals followed by detailed mechanistic in vitro cholinesterase inhibition study. Amongst the series, analogue 13 and 20 are the most promising multi-targeted candidates which can potentially increase memory, decrease free radical levels and protect neurons against cognitive deficit.
Synthesis and evaluation of 2-(substituted phenyl)-4,5-diphenyl-1H-imidazole derivatives as anticonvulsant agents
Maddheshiya, Ashok,Chawla, Pooja
, p. 423 - 427 (2018/09/25)
Some new 1H-imidazole derivatives were synthesized by carrying out reaction between benzil and substituted benzaldehydes and evaluated for anticonvulsant activity by maximum electroshock seizure model. The synthesized compounds were characterized by infrared, mass,1HNMR, and elemental analysis. The compounds were found to possess significant anticonvulsant effects with 3 bearing bromo substitution being the most active compound among the series.
Mixed cobalt/nickel metal–organic framework, an efficient catalyst for one-pot synthesis of substituted imidazoles
Ramezanalizadeh, Hamed,Manteghi, Faranak
, p. 347 - 355 (2017/02/10)
Abstract: In the present work, a three-dimensional bimetallic metal–organic framework, [CoNi(μ3-tp)2(μ2-pyz)2] (tp?=?terephthalic acid, pyz?=?pyrazine) was applied as a highly efficient and recoverable heterogeneous catalyst. The catalyzed reaction was the one-pot three-component condensation reaction between benzil or benzoin with various substituted aromatic aldehydes and ammonium acetate to synthesize the corresponding imidazoles in solvent-free conditions and high to quantitative yields. The catalyst can be recycled at least five times without significant loss in the catalytic activity. To the best of our knowledge, 2,4,5-trisubstituted 1H-imidazoles were not previously synthesized using MOFs as heterogeneous catalyst. The structure of previously reported cobalt/nickel MOF has been confirmed by various techniques, such as X-ray diffraction, thermogravimetric analysis, Fourier transform infrared spectroscopy, field emission scanning electron microscopy, energy dispersive X-ray spectroscopy, and Brunauer–Emmett–Teller. Graphical abstract: [Figure not available: see fulltext.]
Synthesis, photophysical and computational studies of two lophine derivatives with electron-rich substituents in the 2-position
Hamada, Terianne,Le, Tammy,Voegtle, Matthew J.,Doyle, Bryan,Rimby, Jarred,Isovitsch, Ralph
, p. 284 - 290 (2016/11/03)
An exploration of the photophysical properties of two lophine derivatives with electron-donating groups in the 2-position began with the preparation of compounds 1 and 2 via one-pot reactions in good yields, 83% and 74%, respectively. The absorption spect
Identification and Mechanistic Evaluation of Hemozoin-Inhibiting Triarylimidazoles Active against Plasmodium falciparum
Wicht, Kathryn J.,Combrinck, Jill M.,Smith, Peter J.,Hunter, Roger,Egan, Timothy J.
supporting information, p. 201 - 205 (2017/03/08)
In a previous study, target based screening was carried out for inhibitors of β-hematin (synthetic hemozoin) formation, and a series of triarylimidazoles were identified as active against Plasmodium falciparum. Here, we report the subsequent synthesis and testing of derivatives with varying substituents on the three phenyl rings for this series. The results indicated that a 2-hydroxy-1,3-dimethoxy substitution pattern on ring A is required for submicromolar parasite activity. In addition, cell-fractionation studies revealed uncommonly large, dose-dependent increases of P. falciparum intracellular exchangeable (free) heme, correlating with decreased parasite survival for β-hematin inhibiting derivatives.
Copper-mediated C(sp3)-H azidation with Me3SiN3: Synthesis of imidazoles from ketones and aldehydes
Xie, Zeqiang,Deng, Jiaojiao,Qiu, Zhiping,Li, Juan,Zhu, Qiang
supporting information, p. 6467 - 6470 (2016/05/24)
The efficient construction of 2,4,5-trisubstituted imidazoles, through a copper-mediated three-component reaction involving ketones, aldehydes, and Me3SiN3, has been developed. During the process, 4 C-N bonds were formed sequentially. Experimental results and DFT calculations suggested that azidation of the alpha methylene group of the ketone was the key C-N bond-forming step.
