668-94-0Relevant articles and documents
Functionalized Diphenyl-Imidazolo-Pyrimidines
Lyubashov, Pavel P.,Povstyanoy, Vyacheslav M.,Krysko, Andrey A.,Plotkin, Alexander,Lovett, Ilene,Povstyaniy, Mykhailo V.,Lebedyeva, Iryna O.
, p. 276 - 281 (2018)
Synthesis of novel imidazopyrimidines has been reported. These systems contain carbethoxy group at C5 of pyrimidine and bromine at C2 of imidazole. Reactivity of these two groups was studied, and the mobility of the carbethoxy group was confirmed by tracing the formation of the amide product and also with isolation of alkyl analogs while bromine did not react with N-nucleophiles under various reaction conditions employed. New conjugates combine the properties of dihydropyrimidine and imidazole and therefore lead to the expansion of original properties of each heterocyclic moiety within the system.
Synthesis and characterization of new azo 4,5-dimethyl-2-((3-((E)-1-(2- phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole and its metal(II) complexes
Mahmoud, Waleed A.,Musa, Amir,Obaid, Nadia H.
, p. 551 - 555 (2018)
In this paper, a new azo ligand, 4,5-dimethyl-2-((3-((E)-1-(2-phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole (DPDPIH) and its metal complexes were synthesized. The ligand (DPDPIH) and its metal complexes were characterized by elemental, IR, 1H NMR electronic and mass spectra. The values of elemental microanalysis and metal contents were in good agreement with the calculated values. The molar conductivity indicated that all these metal complexes were non-electrolyte in nature. The magnetic susceptibility values indicated that all the metal complexes were paramagnetic except cadmium and zinc complexes.
TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
Asressu, Kesatebrhan Haile,Chan, Chieh-Kai,Wang, Cheng-Chung
, p. 28061 - 28071 (2021/09/15)
In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.
Synthesis method and application of 4, 5-diphenylimidazoline
-
Paragraph 0020-0030, (2020/09/30)
A synthesis method of a chiral compound with a structural formula shown in the specification comprises synthesis, separation and purification. The synthesis is achieved through the following steps: under anhydrous and anaerobic conditions, using 1 mol% of a catalyst palladium complex as a catalyst, weighing 0.5 mmol of azobenzoyl and 5.0 g of ammonium formate, putting the obtained mixture into a 250mL two-neck flask, adding 100 mL of chlorobenzene as a solvent, carrying out a reflux reaction for 30 hours, carrying out column chromatography separation, eluting by using petroleum ether/dichloromethane (1/100), and naturally volatilizing the collected final component point to obtain the monocrystal 4, 5-diphenylimidazoline. The application of the chiral compound (I) shows a certain catalyticeffect in the reaction of benzophenone imine and trimethylsilyl cyanide, and the conversion rate reaches 66%.
Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds
Gabla, Jenifer J.,Lathiya, Dharmesh R.,Revawala, Akash A.,Maheria, Kalpana C.
, p. 1863 - 1881 (2019/01/04)
Abstract: Propylsulfonic acid functionalized Santa Barbara Amorphous-15 (SBA-15–Pr–SO3H) catalyst has been synthesized using a surface modification of mesoporous SBA-15 via the one-pot co-condensation method. The synthesized SBA-15–Pr–SO3H has been characterized by peculiar characterization techniques such as small- and wide-angle XRD, SEM–EDX, TEM, TG–DTA, acidity, FT-IR, Py-FT-IR and BET surface area analysis. The catalytic activity of synthesized catalyst has been studied towards solvent-free MW irradiation for the green and rapid synthesis of multi-substituted imidazoles, [2,4,5-triphenyl-1(H)-imidazole (tri-imidazole) and 1-benzyl-2,4,5-triphenyl-1H-imidazole (tetra-imidazole)]. The SBA-15–Pr–SO3H catalyst was found to be an efficient and recyclable solid acid catalyst and this solvent-free MW protocol afforded products in good to excellent yields of both, tri and tetra imidazoles (> 95%) within shorter reaction time (3?min) at 600?W as compared to the SBA-15 and other existing protocols. The applicability of this protocol was further explored by conducting the experiments in the presence of varied solvents and substituted aldehydes to generate a library of both, tri- and tetra-imidazole scaffolds. The catalyst was found to be reusable up to several runs without loss of its catalytic activity. This report allows the rapid and scalable access to a variety of multi-substituted imidazoles using SBA-15–Pr–SO3H, as heterogeneous catalyst. Graphical abstract: SBA-15–Pr–SO3H catalyzed solvent-free MW assisted green synthesis of multi-substituted imidazoles via MCRs.[Figure not available: see fulltext.].
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.
Design, synthesis and analgesic/anti-inflammatory evaluation of novel diarylthiazole and diarylimidazole derivatives towards selective COX-1 inhibitors with better gastric profile
Abdelazeem, Ahmed H.,El-Saadi, Mohammed T.,Safi El-Din, Asmaa G.,Omar, Hany A.,El-Moghazy, Samir M.
, p. 665 - 676 (2016/12/30)
The inhibition of gastric cyclooxygenase 1 (COX-1) enzyme was believed to be the major cause of non-steroidal anti-inflammatory drugs (NSAIDs)-induced gastric ulcer. Recent studies disproved this belief and showed that the gastric tissues vulnerability is not solely connected to COX-1 inhibition. This work aimed at exploring and rationalizing the differential analgesic and anti-inflammatory activities of novel selective COX-1 inhibitors with improved gastric profile. Two novel series of 4,5-diarylthiazole and diarylimidazole were designed, synthesized in analogy to selective COX-1 inhibitors (mofezolac and FR122047) which lack gastric damaging effects. The new compounds were evaluated in vitro for their COXs inhibitory activity and in vivo for their anti-inflammatory and analgesic potentials. Four compounds; diphenylthiazole glycine derivatives (15a, 15b) and diphenylimidazolo acetic acid derivatives (19a, 19b), which possess carboxylic acid group exhibited significant activity and selectivity against COX-1 over COX-2. Of these compounds, (4,5-bis(4-methoxyphenyl)thiazol-2-yl)glycine 15b was the most potent compound against COX-1 with an inhibitory half maximal concentration (IC50) of 0.32 μM and a selectivity index (COX-2 IC50/COX-1 IC50) of 28.84. Furthermore, an ulcerogenicity study was performed where the tested compounds demonstrated a significant gastric tolerance. Interestingly, the most selective COX-1 inhibitor showed higher analgesic activity in vivo as expected compared to their moderate anti-inflammatory activity. This study underscores the need for further design and development of novel analgesic agents with low tendency to cause gastric damage based on improving their COX-1 affinity and selectivity profile.
A mechanistic study of carbonyl activation under solvent-free conditions: Evidence drawn from the synthesis of imidazoles
Pradhan, Kiran,Tiwary, Bipransh Kumar,Hossain, Mossaraf,Chakraborty, Ranadhir,Nanda, Ashis Kumar
, p. 10743 - 10749 (2016/02/05)
Syntheses of various imidazoles and their derivatives, imidazole N-oxides and 1-hydroxyimidazole 3-oxides, from sterically different dicarbonyl moieties provided insights into the self-catalytic effect of the condensed phase reactions of carbonyl compounds. The self-catalytic activity in solvent-free multi-component syntheses was investigated using a combination of methods viz., reactivity, spectroscopy and theory. While IR spectroscopic studies revealed that reacting molecules were polarised in bulk, quantum mechanical calculations of associated HCHO monomers suggest an increase in the average dipole moment of each monomer and provide evidence for the presence of cooperative effects. A comparative study of the kinetics of un-catalysed and catalysed reactions with the help of HPLC provided insights into the mechanism.
Simple and efficient method for the synthesis of highly substituted imidazoles catalyzed by benzotriazole
Xu, Feng,Wang, Nige,Tian, Youping,Li, Gaoqiang
, p. 668 - 675 (2013/06/27)
Benzotriazole is an efficient, readily available, and simple catalyst for the synthesis of 2,4,5-trisubstituted imidazoles in high yields from 1,2-diketones and aldehydes in the presence of NH4OAc via multi-components reaction. The significant features of this one-pot procedure are very simple operation, easy work-up and purification of products.
