Design, synthesis, and biological evaluation of novel imidazole derivatives possessing terminal sulphonamides as potential BRAFV600Einhibitors

Ali, Eslam M.H.; Abdel‐Maksoud, Mohammed S.; Ammar, Usama M.; Mersal, Karim I.; Yoo, Kyung Ho; Jooryeong, Park; Oh, Chang‐Hyun

doi:10.1016/j.bioorg.2020.104508

Cited by 26 publications

(23 citation statements)

References 39 publications

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“…[2,3] The heterocyclic derivatives of imidazole (C 3 H 4 N 2 ), which is an important member of the heterocyclic aromatic compounds, have been widely studied in the field of pharmaceutical chemistry and other fields due to their versatile use and various biological activities. [4][5][6][7][8] Thiadiazole is a heterocyclic aromatic compound that has a five-member ring with 2 nitrogen atoms and one sulfur atom, in addition to carbon and hydrogen atoms. There are four different isomers of thiadiazoles named 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole, according to the Hantzsch-Widman nomenclature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Tunel

Alıcı

et al. 2021

Journal of Heterocyclic Chem

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In this study, thioether-bridged imidazo [2,1-b][1,3,4]thiadiazole derivatives that contained both imidazole and 1,3,4-thiadiazole (compounds 7a-7i and 8a-8i) were synthesized from the reactions of 2-amino-1,3,4-thiadiazole with phenacyl bromide (6a-6i) (at yields of 59% to 74%). The structure of the synthesized compounds was characterized using 1 H NMR, 13 C NMR, Fouriertransform infrared spectroscopy, elemental analysis, mass spectroscopy, and Xray diffraction analysis. Mycelial growth, mycelial growth inhibition, minimum inhibitory concentration, minimum fungicidal concentration, and lethal dose values against various plant pathogenic fungi were determined for all of the target compounds synthesized in the study. The test results showed that most of the compounds had moderate to good antifungal activity. In addition, the absorption, distribution, metabolism, excretion (ADME) parameters of the compounds were calculated, and it was observed that all of the compounds met the drug-likeness rules in general. Finally, using docking simulations, it was found that compounds 7h, 7i, 8h, and 8i showed high affinity to PDB ID:5TZ1, which is an CYP51 antifungal target structure.

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Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Tunel

Alıcı

et al. 2021

Journal of Heterocyclic Chem

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“…Anticancer activity of the azole derivatives is most extensively studied and some of them are in clinical practice as antitumor active agents [4,5]. Imidazoles are an important class of heterocyclic molecules and imidazole derivatives are reported to have anticancer activity [6][7][8]. Misonidazole I displayed superior antiproliferative activity against a panel of cancer cell lines [9].…”

Section: Introductionmentioning

confidence: 99%

“…General Procedure for the Synthesis (E)-2-((3-Acetyl-5-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1H-imidazol-1-ylimino)methyl)phenyl Acetate(6) …”

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confidence: 99%

5-Aryl-1-Arylideneamino-1H-Imidazole-2(3H)-Thiones: Synthesis and In Vitro Anticancer Evaluation

et al. 2021

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A novel series of N-1 arylidene amino imidazole-2-thiones were synthesized, identified using IR, 1H-NMR, and 13C-NMR spectral data. Cytotoxic effect of the prepared compounds was carried out utilizing three cancer cell lines; MCF-7 breast cancer, HepG2 liver cancer, and HCT-116 colon cancer cell lines. Imidazole derivative 5 was the most potent of all against three cell lines. DNA flow cytometric analysis showed that, imidazoles 4d and 5 exhibit pre-G1 apoptosis and cell cycle arrest at G2/M phase. The results of the VEGFR-2 and B-Raf kinase inhibition assay revealed that compounds 4d and 5 displayed good inhibitory activity compared with reference drug erlotinib.

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“…Compound C13 possesses a potential anti-cancer activity against both NCI 60 and melanoma human cancer cell lines via BRAF V600E kinase inhibition. 23 …”

Section: Anti-cancer Properties Of Imidazole Derivativesmentioning

confidence: 99%

“…Compound C13 possesses a potential anti-cancer activity against both NCI 60 and melanoma human cancer cell lines via BRAF V600E kinase inhibition. 23 In a work reported in 2020, anti-cancer activity of a newly synthesized novel imidazole derivatives was investigated against multiple cancer cell lines including human colon carcinoma (Caco-2 and HCT-116), human cervical carcinoma (HeLa), and human breast adenocarcinoma (MCF-7). Compound C14 demonstrated the highest cytotoxic activity against all cancer cell lines specifically against MCF-7 with IC 50 0.38 μM.…”

Section: Anti-cancer Properties Of Imidazole Derivativesmentioning

confidence: 99%

Imidazole as a Promising Medicinal Scaffold: Current Status and Future Direction

Alghamdi¹,

Suliman²,

Almutairi³

et al. 2021

DDDT

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Various imidazole-containing compounds have been tested for their medical usefulness in clinical trials for several disease conditions. The rapid expansion of imidazole-based medicinal chemistry suggests the promising and potential therapeutic values of imidazole-derived compounds for treating incurable diseases. Imidazole core scaffold contains three carbon atoms, and two nitrogen with electronic-rich characteristics that are responsible for readily binding with a variety of enzymes, proteins, and receptors compared to the other heterocyclic rings. Herein, we provide a thorough overview of the current research status of imidazole-based compounds with a wide variety of biological activities including anti-cancer, anti-microbial, anti-inflammatory and their potential mechanisms including topoisomerase IIR catalytic inhibition, focal adhesion kinase (FAK) inhibition, c-MYC G-quadruplex DNA stabilization, and aurora kinase inhibition. Additionally, a great interest was reported in the discovery of novel imidazole compounds with anti-microbial properties that break DNA double-strand helix and inhibit protein kinase. Moreover, anti-inflammatory mechanisms of imidazole derivatives include inhibition of COX-2 enzyme, inhibit neutrophils degranulation, and generation of reactive oxygen species. This systemic review helps to design and discover more potent and efficacious imidazole compounds based on the reported derivatives, their ADME profiles, and bioavailability scores that together aid to advance this class of compounds.

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Design, synthesis, and biological evaluation of novel imidazole derivatives possessing terminal sulphonamides as potential BRAFV600Einhibitors

Cited by 26 publications

References 39 publications

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

5-Aryl-1-Arylideneamino-1H-Imidazole-2(3H)-Thiones: Synthesis and In Vitro Anticancer Evaluation

Imidazole as a Promising Medicinal Scaffold: Current Status and Future Direction

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