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Synthesis and Anticancer Activity of New Pyridine-Thiophene and Pyridine-Furan Hybrid Compounds, Their Sugar Hydrazone, and Glycosyl Derivatives

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Abstract

New sugar hydrazones and their derived oxadiazolyl acyclic nucleoside analogs in addition to the derived thioglycosides incorporating pyridine, furan or thiophene have been synthesized via a multi-component reaction (MCR). The acetylated derivatives of hydrazones and the derived deprotected thioglycosides of the prepared acetylated analogs have been also synthesized. Anticancer activity of the products has been tested against adenocarcinomic human alveolar basal epithelial (A549), human prostatic adenocarcinoma (PC3) and human colorectal carcinoma (HCT116) cell lines in addition to their effect on human normal retinal pigmented epithelial cell line (RPE1) using the MTT assay. Three products: acid hydrazide, sugar hydrazine and glycoside are characterized by high activity against three cancer cell lines.

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REFERENCES

  1. Li, T., Zhang, J., Pan, J., Wu, Z., Hu, D., and Song, B., Eur. J. Med. Chem., 2017, vol. 125, p. 657. https://doi.org/10.1016/j.ejmech.2016.09.069

  2. El-Sayed, W., Khalaf, H., Mohamed, S., Hussien, H., Kutkat, O., and Amr, A., Russ. J. Gen. Chem., 2017, vol. 87, p. 2444. https://doi.org/10.1134/S1070363217100279

  3. Nassar, I.F., El-Sayed, W.A., Ragab, T.I., Shalaby, A.S.G., and Mehany, A., Mini Rev. Med. Chem., 2019, vol. 19, p. 395. https://doi.org/10.2174/1389557518666180820125210

  4. Stegmeier, F., Warmuth, M., Sellers, W., and Dorsch, M., Clin. Pharmacol. Ther., 2010, vol. 87, p. 543. https://doi.org/10.1038/clpt.2009.297

  5. Fadda, A., Abdel-Rahman, A.-H., El-Sayed, W., Zidan, T., and Badria, F., Chem. Heterocycl. Compd., 2011, vol. 47, p. 856. https://doi.org/10.1007/s10593-011-0847-4

  6. El-Essawy, F., El-Sayed, W., El-Etrawy, A.S., and El-Bayaa, M.,Chem. Heterocycl. Compd., 2013, vol. 48, p. 1853. https://doi.org/10.1007/s10593-013-1219-z

  7. El-Sayed, W.A., Metwally, M.A., Nada, D.S., Mohamed, A.A., and Abdel-Rahman, A.A.H., J. Heterocycl. Chem., 2013, vol. 50, p. 194. https://doi.org/10.1002/jhet.901

  8. Dewick, P.M., Medicinal Natural Products: A Biosynthetic Approach, New York: John Wiley and Sons, 2002. https://doi.org/10.1002/0470846275

  9. Mabkhot, Y.N., Alatibi, F., El-Sayed, N.N.E., Al-Showiman, S., Kheder, N.A., Wadood, A., Rauf, A., Bawazeer, S., and Hadda, T.B., Molecules, 2016, vol. 21, p. 222. https://doi.org/10.3390/molecules21020222

  10. Mbaveng, A.T., Sandjo, L.P., Tankeo, S.B., Ndifor, A.R., Pantaleon, A., Nagdjui, B.T., and Kuete, V., Springer Plus, 2015, vol. 4, p. 823. https://doi.org/10.1186/s40064-015-1645-8

  11. Ajdačić, V., Senerovic, L., Vranić, M., Pekmezovic, M., Arsic-Arsnijevic, V., Veselinovic, A., Veselinovic, J., Šolaja, B.A., Nikodinovic-Runic, J., and Opsenica, I.M., Bioorg. Med. Chem., 2016, vol. 24, p. 1277. https://doi.org/10.1016/j.bmc.2016.01.058

  12. Leitans, J., Sprudza, A., Tanc, M., Vozny, I., Zalubovskis, R., Tars, K., and Supuran, C.T., Bioorg. Med. Chem., 2013, vol. 21, p. 5130. https://doi.org/10.1016/j.bmc.2013.06.041

  13. da Franca Rodrigues, K.A., de Sousa Dias, C.N., do Nascimento Neris, P.L., da Câmara Rocha, J., Scotti, M.T., Scotti, L., Mascarenhas, S.R., Veras, R.C., de Medeiros, I.A., and Keesen, T.D.S.L., Eur. J. Med. Chem., 2015, vol. 106, p. 1. https://doi.org/10.1016/j.ejmech.2015.10.011

  14. Basiony, E.A., Hassan, A.A., Al-Amshany, Z.M., Abd-Rabou, A.A., Abdel-Rahman, A.A.-H., Hassan, N.A., and El-Sayed, W.A., Molecules, 2020, vol. 25, p. 399. https://doi.org/10.3390/molecules25020399

  15. Romagnoli, R., Baraldi, P.G., Kimatrai Salvador, M., Preti, D., Aghazadeh Tabrizi, M., Bassetto, M., Brancale, A., Hamel, E., Castagliuolo, I., and Bortolozzi, R., J. Med. Chem., 2013, vol. 56, p. 2606. https://doi.org/10.1021/jm400043d

  16. Kao, C.-L. and Chern, J.-W., Tetrahedron Lett., 2001, vol. 42, p. 1111. https://doi.org/10.1016/S0040-4039(00)02163-8

  17. El-Sayed, W.A., Ramiz, M.M., and Adel, A.-H., Monatsh. Chem., 2008, vol. 139, p. 1499. https://doi.org/10.1007/s00706-008-0941-1

  18. El-Sayed, W.A., Abbas, H.A.S., Mohamed, A.M., and Abdel-Rahman, A.A.H., J. Heterocycl. Chem., 2011, vol. 48, p. 1006. https://doi.org/10.1002/jhet.679

  19. Coşkun, D., Tekin, S., Sandal, S., and Coşkun, M.F., J. Chem., 2016, vol. 2016. https://doi.org/10.1155/2016/7678486

  20. El-Sayed, W.A. and Adel, A.-H., Z. Naturforsch. B, 2010, vol. 65, p. 57. https://doi.org/10.1515/znb-2010-0110

  21. Ali, O.M., El-Sayed, W.A., Eid, S.A., Abdelwahed, N., and Abdel-Rahman, A., Acta Pol. Pharm., 2012, vol. 69, p. 657. PMID: 22876608

  22. Kassem, A.F., Nassar, I.F., Abdel-Aal, M.T., Awad, H.M., and El-Sayed, W.A., Chem. Pharm. Bull., 2019, vol. 67, p. 888. https://doi.org/10.1248/cpb.c19-00280

  23. El Ashry, E.S. and El Kilany, Y., Adv. Heterocycl. Chem., 1998, 69, p. 129. https://doi.org/10.1016/S0065-2725(08)60082-3

  24. Rahman, A.A., Nassar, I.F., Shaban, A.K., El-Kady, D.S., Awad, H.M., and El Sayed, W.A., Mini Rev. Med. Chem., 2019, vol. 19, p. 1093. https://doi.org/10.2174/1389557519666190312165717

  25. Alminderej, F.M., Elganzory, H.H., El-Bayaa, M.N., Awad, H.M., and El-Sayed, W.A., Molecules, 2019, vol. 24, p. 3738. https://doi.org/10.3390/molecules24203738

  26. Kassem, A.F., Abbas, E.M., El-Kady, D.S., Awad, H.M., and El-Sayed, W.A., Mini Rev. Med. Chem., 2019, vol. 19, p. 933. https://doi.org/10.2174/1389557519666181231121217

  27. El-Sayed, W.A., Osman, D.A., Khalaf, H.S., Abbas, H.-A.S., and Ali, M.M., Acta Pol. Pharm., 2017, vol. 74, p. 1739.

  28. Attia, A. and Michael, M., Chemischer Informationsdienst, 1983, vol. 14. https://doi.org/10.1002/chin.198336230

  29. Attia, A. and Kamel, M., J. Cheminf., 1988, vol. 19. https://doi.org/10.1002/chin.198806187

  30. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, p. 55. https://doi.org/10.1016/0022-1759(83)90303-4

  31. El-Sayed, W.A., Mohamed, A.M., Khalaf, H.S., ElKady, D.S., and Al-Manawaty, M., J. Appl. Pharm., 2017, vol. 7, p. 001. https://doi.org/10.7324/JAPS.2017.70901

  32. Vogel, A.I., Tatchell, A.R., Furnis, B.S., Hannaford, A.J., and Smith, P.W.G., Vogel’s Textbook of Practical Organic Chemistry, New York: Wiley, 1989, p. 647.

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Authors and Affiliations

  1. Photochemistry Department, National Research Centre, 12622, Giza, Dokki, Egypt

    H. S. Khalaf, H. E. M. Tolan, M. N. El-Bayaa & W. A. El-Sayed

  2. Chemistry Department, College of Science and Arts-Qurayat, Jouf University, 42421, Sakaka, Saudi Arabia

    H. S. Khalaf

  3. Applied Organic Chemistry Department, National Research Center, 12622, Giza, Dokki, Egypt

    M. A. A. Radwan

  4. Department of Chemistry, Collage of Science, Qassim University, 51452, Buridah, Saudi Arabia

    M. A. A. Radwan & W. A. El-Sayed

  5. Pharmacognosy Department, National Research Centre, 12622, Giza, Dokki, Egypt

    M. El-Manawaty

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  1. H. S. Khalaf
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  2. H. E. M. Tolan
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  3. M. N. El-Bayaa
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Correspondence to M. N. El-Bayaa or W. A. El-Sayed.

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Khalaf, H.S., Tolan, H.E.M., El-Bayaa, M.N. et al. Synthesis and Anticancer Activity of New Pyridine-Thiophene and Pyridine-Furan Hybrid Compounds, Their Sugar Hydrazone, and Glycosyl Derivatives. Russ J Gen Chem 90, 1706–1715 (2020). https://doi.org/10.1134/S1070363220090182

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