Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole combined Glucosides with coumarin
Main Article Content
Keywords
Carbohydrate, 4-hydroxy coumarin, Click chemistery,1,2,3-triazole
Abstract
The synthetic strategy for the preparation of the targeted glycosides involved two different pathways to obtain two types of hybrid compounds; the first represents new 1,2,3-triazole derivative in the 6-carbon glucopyranose, and the other is a new glycoside of 4-hydroxy coumarin bases. The starting derivative 1 prepared by reaction of 6-azide glucopyranose and 2 ethylene azide-2,3,4,6-tetraacetate- β-D- glucopyranoside with propargyl 4-hydroxy coumarin under click conditions .The cytotoxicity potentials of glucosides derivatives were evaluated by MTT assay against liver cancer primary tissue culture , which appear that derivatives exhibited selective cytotoxicity against liver cancer cells isolated from Iraqi patients with inhibitory concentration (IC50) 106.81 μg/ml. Docking simulation studies were performed to check the binding patterns of the synthesized compounds. Enzyme inhibition assay studies were also conducted for the epidermal growth factor receptor (EGFR), and the results explained the activity of a number of derivatives.
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2. A. F. Razaq and M. J. Mohammed, “Synthesis and Studying of the Biological Activity of Some New Coumarin-3-carboxylic Acid Heterocyclic Derivatives, Egypt. J. Chem., 2022, 65, 2, pp. 35–40.
3. M. M. Heravi, S. Khaghaninejad, and M. Mostofi, Pechmann reaction in the synthesis of coumarin derivatives,” in Advances in heterocyclic chemistry, 2014 , 112, Elsevier, , pp. 1–50.
4. M. Tolba et al., “An overview on synthesis and reactions of coumarin based compounds, Curr. Chem. Lett., 2022, 11, 1, pp. 29–42.
5. A. S. Barrow, C. J. Smedley, Q. Zheng, S. Li, J. Dong, and J. E. Moses, The growing applications of SuFEx click chemistry,” Chem. Soc. Rev., 2019 ,48, 17, pp. 4731–4758.
6. S. I. Presolski, V. P. Hong, and M. G. Finn, Copper‐catalyzed azide–alkyne click chemistry for bioconjugation,” Curr. Protoc. Chem. Biol., 2011 , 3, 4, pp. 153–162.
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8. M. S. Singh, S. Chowdhury, and S. Koley, “Advances of azide-alkyne cycloaddition-click chemistry over the recent decade , Tetrahedron, 2016 , 72, 35, pp. 5257-5283
9. E. Bonandi, M. S. Christodoulou, G. Fumagalli, D. Perdicchia, G. Rastelli, and D. Passarella, “The 1, 2, 3-triazole ring as a bioisostere in medicinal chemistry, Drug Discov. Today, 2017 , 22, ,10, pp. 1572–1581.
10. F. Wei, W. Wang, Y. Ma, C.-H. Tung, and Z. Xu, “Regioselective synthesis of multisubstituted 1, 2, 3-triazoles: moving beyond the copper-catalyzed azide–alkyne cycloaddition, Chem. Commun., 2016 , 52, 99, pp. 14188–14199..
11. R. S. Gomes, G. A. M. Jardim, R. L. de Carvalho, M. H. Araujo, and E. N. da Silva Júnior, “Beyond copper-catalyzed azide-alkyne 1, 3-dipolar
cycloaddition: Synthesis and mechanism insights, Tetrahedron, 2019 , 75, 27, pp. 3697–3712.
12. J. El-Abid, V. Moreau, J. Kovensky, and V. Chagnault, “Effects of CoCl2 on the regioselective tosylation of oligosaccharides, J. Mol. Struct., 2021 ,1241, p. 130609.
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14. Z. D. Wang, Y. Mo, C.-L. Chiou, and M. Liu, “A simple preparation of 2, 3, 4, 6-tetra-O-acyl-gluco-, galacto-and mannopyranoses and relevant theoretical study, Molecules, 2010. 15, 1, pp. 374–384.
15. M. M. Zeydi, S. J. Kalantarian, and Z. Kazeminejad, “Overview on developed synthesis procedures of coumarin heterocycles, J. Iran. Chem. Soc., 2020., 17, 12, pp. 3031–3094.
16. S. Hao et al., “Design, synthesis and biological evaluation of novel carbohydrate-based sulfonamide derivatives as antitumor agents, Bioorg. Chem., 2020 ,104, p. 104237.
17. V. Aragão-Leoneti, V. L. Campo, A. S. Gomes, R. A. Field, and I. Carvalho, “Application of copper (I)-catalysed azide/alkyne cycloaddition (CuAAC)‘click chemistry’in carbohydrate drug and neoglycopolymer synthesis, Tetrahedron, 2010. 66, 49, pp. 9475–9492.
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23. S. Release, “4: LigPrep, Schrödinger, 2019.LLC, New York, NY.
24. A. C. Kaushik, D. Gautam, A. S. Nangraj, D.-Q. Wei, and S. Sahi, “Protection of primarydopaminergic midbrain neurons through impact of small molecules using virtual screening of gpr139 supported by molecular dynamic simulation and systems biology, Interdiscip. Sci. Comput. Life Sci., 2019. 11, 2, pp. 247–257.
25. L. K. Williams, C. Li, S. G. Withers, and G. D. Brayer, “Order and disorder: differential structural impacts of myricetin and ethyl caffeate on human amylase, an antidiabetic target, J. Med. Chem., 2012, 55, 22, pp. 10177–10186.
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27. C.-F. Liu, Q.-K. Shen, J.-J. Li, Y.-S. Tian, and Z. Quan, “Synthesis and biological evaluation of novel 7-hydroxy-4-phenylchromen-2-one–linked to triazole moieties as potent cytotoxic agents, J. Enzyme Inhib. Med. Chem., 2017. 32, 1, pp. 1111–1119.
28. T. Hayon, A. Dvilansky, O. Shpilberg, and I. Nathan, “Appraisal of the MTT-based assay as a useful tool for predicting drug chemosensitivity in leukemia, Leuk. Lymphoma, 2003, 44, 11, pp. 1957–1962.
29. S. Kasibhatla, G. P. Amarante-Mendes, D. Finucane, T. Brunner, E. Bossy-Wetzel, and D. R. Green, “Acridine orange/ethidium bromide (AO/EB) staining to detect apoptosis,” Cold Spring Harb. Protoc., 2006, 3, p. 4493..
30. H. E. Hashem, A. E.-G. E. Amr, E. S. Nossier, M. M. Anwar, and E. M. Azmy, “New benzimidazole-, 1, 2, 4-triazole-, and 1, 3, 5-triazine-based derivatives as potential EGFRWT and EGFRT790M inhibitors: microwave-assisted synthesis, anticancer evaluation, and molecular docking study, ACS omega, 2022, 7, 8, pp. 7155–7171.
31. H. S. Mohammed, S. William, T. Aboushousha, H. M. A. Taleb, R. Sabour, and M. A. Ghareeb, “Ailanthus excelsa leaf extract: Chemical characterization, antischistosomal activity, and in silico study of isolated phenolic compounds as promising thioredoxin glutathione reductase inhibitors,,J. Appl. Pharm. Sci., 2023,13, 2, pp. 124–145.
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May 6, 2023
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How to Cite
Ruaa Wassim Adam, & Ezzat Hussein Zimam. (2023). Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole combined Glucosides with coumarin. Journal of Population Therapeutics and Clinical Pharmacology, 30(9), 345-356. https://doi.org/10.47750/jptcp.2023.30.09.035
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All articles published in JPTCP are licensed under Copyright Creative Commons Attribution-NonCommercial 4.0 International License.
How to Cite
Ruaa Wassim Adam, & Ezzat Hussein Zimam. (2023). Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole combined Glucosides with coumarin. Journal of Population Therapeutics and Clinical Pharmacology, 30(9), 345-356. https://doi.org/10.47750/jptcp.2023.30.09.035