One-Pot Synthesis of Tetra Substituted Imidazoles Catalyzed by Fly Ash Supported Bi2O3–ZnO

Ezhilmathi, P.; Thirumalai, K.; Swaminathan, M.; Krishnasamy, K.

doi:10.1166/jnn.2019.16863

Cited by 8 publications

(7 citation statements)

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“…Different primary amines of both aliphatic and substituted aromatic units were used to generate tetra‐substituted imidazoles as explained in Scheme 2. Compounds 5 b , 5 d , 5 e , and 5 f were synthesized by employing the respective primary amines as additional starting materials by following a similar procedure as described earlier [25–27] . These compounds were then purified using a similar way as compound 5 a .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Exploration of N‐Tetra‐Substituted Imidazoles as Effective Agents To Counteract Gastric Cancer Cell Viability: Synthesis and Biological Evaluation

Ganesh,

Aruchamy,

Ramani

et al. 2023

ChemistrySelect

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The tetra‐substituted imidazole offers more possibilities for modification and functionalization, allowing for fine‐tuning of the compound‘s biological activity. The substituents attached to the imidazole ring can be strategically chosen to introduce specific functional groups, steric effects, or electronic properties, thereby influencing the compound‘s overall bioactivity. An efficient one‐pot synthesis of 2,4,5‐tri and 1,2,4,5‐tetrasubstituted imidazoles was performed, which involves benzyl (1,2‐diphenylethane‐1,2‐dione), N‐methyl pyrrole‐2‐carboxaldehyde, appropriate primary amine, ammonium acetate, and iodine as a catalyst. The N‐alkylation on the imidazole was performed to introduce alkyl chains. All six synthesized compounds were purified, characterized using spectroscopic techniques, and tested against the primary Human Gingival Fibroblasts (HGFs) and AGS gastric adenocarcinoma cell line to assess their effect on cell viability. All the tested molecules displayed a low percentage of dead cells >50 μM on HGFs; compounds 1‐butyl‐2‐(1‐methyl‐1H‐pyrrol‐2‐yl)‐4,5‐diphenyl‐1H‐imidazole (5b) and 2‐(1‐methyl‐1H‐pyrrol‐2‐yl)‐1‐pentyl‐4,5‐diphenyl‐1H‐imidazole (5c) have demonstrated a remarkable ability to counteract cell viability than the other compounds, specifically on AGS cells, up to a concentration of 10 μM. This suggests that these two compounds have a higher potency in reducing the viability of AGS cells than the other tested compounds. These results align with current studies highlighting the enhanced anticancer efficacy of imidazole‐pyrrole hybrids against AGS cell line.

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Section: Resultsmentioning

confidence: 99%

“…Compounds 5 b, 5 d, 5 e, and 5 f were synthesized by employing the respective primary amines as additional starting materials by following a similar procedure as described earlier. [25][26][27] These compounds were then purified using a similar way as compound 5 a.…”

Section: Chemistrymentioning

confidence: 99%

Exploration of N‐Tetra‐Substituted Imidazoles as Effective Agents To Counteract Gastric Cancer Cell Viability: Synthesis and Biological Evaluation

Ganesh,

Aruchamy,

Ramani

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

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“…wide-ranging catalyst and reaction conditions have been described in literature. For instance, Nano-TiCl 4 .SiO 2 , [16] SiO 2 -Pr-SO 3 H, [17] ZnFe 2 O 4 magnetic nanoparticles, [18] fly ash loaded Bi 2 O 3 -ZnO, [19] zeolite HY and silica gel under microwave irradiation, [20] Trityl chloride (TrCl or Ph 3 CCl) under neutral and solvent-free conditions, [21] and Preyssler-type heteropoly acid catalyst. [22] On the other hand, tetrasubstituted imidazoles was also reported via a photochemical catalyzed three component reaction (aldehydes, α-aminonitriles, and isoxazoles) [23] or from phosphonite PPh(catechyl) mediated imines, acid chlorides, and N-nosyl imines or tethered nitriles reaction [24] Furthermore, many two component reactions have been reported like oxidative coupling of amidines and chalcones that catalyzed by FeCl 3 /I 2 [25] or sequential reaction of allenyl sulfonamides and amines.…”

Section: Chemistrymentioning

confidence: 99%

Tailored Tetrasubstituted Imidazole Carrying the Benzenesulfonamide Fragments as Selective Human Carbonic Anhydrase IX/XII Inhibitors

Taher,

Marzouk,

Abd‐Allah

et al. 2024

ChemMedChem

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A new series of tetrasubstituted imidazole carrying sulfonamide as zinc‐anchoring group has been designed. The structures of the synthesized derivatives 5a‐l have been confirmed by spectroscopic analysis. These compounds incorporate an ethylenic spacer between the benznesulfonamide and the rest of the trisubstituted imidazole moiety and were tested as inhibitors of carbonic anhydrases and for invitro cytotoxicity. Most of them act as effective inhibitors of the tumor‐linked CA isoforms IX and XII, in nanomolar range. Also, different compounds have shown selectivity in comparable with the standard acetazolamide. Our IBS 5d, 5g, and 5l (with Ki: 10.1, 19.4, 19.8 nM against hCA IX and 47, 45, 20 nM against hCA IX, compounds 5d, 5g, 5h and 5l Ki: 46.7, 45.9, 15.5 and 20.1 nM, respectively) showed the best inhibitory profile. In‐vitro screening of all derivatives against a full sixty‐cell‐lined from NCI at a single dose of 10 μM offered growth inhibition of up to 45 %. Compound 5b has been identified with the most potent cytotoxic activity and broad spectrum. Docking studies have also been implemented and were also in accordance with the biological outcomes. Our SAR analysis has interestingly proposed efficient tumor‐related hCAs IX/XII suppression.

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“…While the main four reaction components are well defined, a wide variety of reaction catalysts and conditions have been reported. For example, the readily available and reusable nano-TiCl 4 .SiO 2 , [28] SiO 2 À PrÀ SO 3 H, [29] ZnFe 2 O 4 magnetic nanoparticles, [30] fly ash loaded Bi 2 O 3 À ZnO, [31] zeolite HY and silica gel under microwave irradiation, [32] trityl chloride (TrCl or Ph 3 CCl) under neutral and solvent-free conditions, [33] and Preyssler-type heteropoly-acid catalyst. [34] Interestingly, further methods that utilize fewer than four components have also been reported, such as the photochemical one-pot threecomponent synthesis (from aldehydes, α-aminonitriles, and isoxazoles) of tetrasubstituted imidazoles, [35,36] from amidines and chalcones via FeCl 3 /I 2 -catalyzed aerobic oxidative coupling, [37] sequential reaction of allenyl sulfonamides and amines, [38] from imines, acid chlorides, and N-nosyl imines or ChemMedChem tethered nitriles and mediated by the phosphonitePPh(catechyl) [39] alkylation of synthesized NH imidazoles with alkyl halide.…”

Section: Chemistrymentioning

confidence: 99%

Anticancer Activities of Tetrasubstituted Imidazole‐Pyrimidine‐Sulfonamide Hybrids as Inhibitors of EGFR Mutants

et al. 2023

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A new series of tetrasubstituted imidazole derivatives carrying pyrimidine sulfonamide pharmacophores has been synthesized and evaluated for their anticancer activities. In‐vitro screening of these hybrids against a full 60‐cell‐line panel at a single dose of 10 μM showed significant growth inhibition of up to 95 %. The most active compound showed in‐vitro anticancer activities against (i) abnormal HER2 and (ii) two mutants for EGFR. Apoptotic gene expression revealed that lead compounds induced MCF‐7 cell line apoptosis together with considerable change in the Bax/Bcl‐2 expression ratio. One lead compound led to a significant cell‐cycle S‐phase arrest, while another blocked the cell cycle at G1/S‐phase causing the accumulation of cells. Docking analysis of these two hybrids adopted the orientation and binding interactions with a higher liability to enter the active side pocket of HER2, L858R, and T790 M, preferable to that of co‐crystallized ligands. Modelling simulation was consistent with the acquired biological evaluation.

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One-Pot Synthesis of Tetra Substituted Imidazoles Catalyzed by Fly Ash Supported Bi2O3–ZnO

Cited by 8 publications

References 0 publications

Exploration of N‐Tetra‐Substituted Imidazoles as Effective Agents To Counteract Gastric Cancer Cell Viability: Synthesis and Biological Evaluation

Exploration of N‐Tetra‐Substituted Imidazoles as Effective Agents To Counteract Gastric Cancer Cell Viability: Synthesis and Biological Evaluation

Tailored Tetrasubstituted Imidazole Carrying the Benzenesulfonamide Fragments as Selective Human Carbonic Anhydrase IX/XII Inhibitors

Anticancer Activities of Tetrasubstituted Imidazole‐Pyrimidine‐Sulfonamide Hybrids as Inhibitors of EGFR Mutants

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