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Synthesis and Anticancer Activity of New 1,3,4-Thiadiazolyl-1,2,4-Triazolyl and 1,3,4-Oxadiazolyl Hybrids, Their Thioglycosides, and Acyclic Analogs

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Abstract

New Furan, 1,3,4-thiadiazole and 1,2,4-triazole hybrid compounds and their 1,3,4-oxadiazole hybrid derivatives were synthesized. The thioglycoside derivatives of the synthesized hybrid compounds were synthesized via glycosylation of the triazole-5-thione and 1,3,4-oxadiazole-5-thione derivatives. The hydrazinyl sugar derivative of the thiadiazole system and hydroxyalkylamino derivative of the 1,2,4-triazole compound were also prepared. The cytotoxic activities of the synthesized compounds were studied against MCF-7 (human breast adenocarcinoma) cancer cell and RPE-1 (human normal Retina pigmented epithelium) cell lines using the MTT assay. The obtained results showed that a number of the synthesized compounds revealed good activities comparable to that observed for the reference drug doxorubicin against the MCF-7 cancer cell lines.

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REFERENCES

  1. Jemal, A., Siegel, R., Ward, E., Hao, Y., Xu, J., Murray, T., and Thun, M., Cancer Statistics, CA Cancer J. Clin., 2008, vol. 58, pp. 71–96. https://doi.org/10.3322/CA.2007.0010

    Article  PubMed  Google Scholar 

  2. Haskell, C.M., Cancer Treatment, Philadelphia, PA: Saunders, 2001, Ch. 1, 5th ed.

    Google Scholar 

  3. Decker, M., Design of Hybrid Molecules for Drug Development, London, UK: Elsevier, 2017.

    Google Scholar 

  4. Wilton-Ely, J.D.E.T., Schier, A., and Schmidbaur, H., Organometallics, 2001, vol. 20, pp. 1895–1897. https://doi.org/10.1021/om010099y

    Article  CAS  Google Scholar 

  5. Bentiss, F., Lagrene’e, M., Wignacourt, J.P., and Holt, E.M., Polyhedron, 2002, vol. 21, pp. 403–408. https://doi.org/10.1016/S0277-5387(01)01012-9

    Article  CAS  Google Scholar 

  6. Aliabadi, A., Anticancer Agents Med. Chem., 2016, vol. 16, pp. 1301–1314. https://doi.org/10.2174/1871520616666160628100936

    Article  CAS  PubMed  Google Scholar 

  7. Flefel, E.M., El-Sayed, W.A., Mohamed, A.M., El-Sofany, W.I., and Awad, H.M., Molecules, 2017, vol. 22, pp. 170. https://doi.org/10.3390/molecules22010148

    Article  CAS  PubMed Central  Google Scholar 

  8. Padmavathi, V., Sudhakar, R. G., Padmaja, A., Kondaiah P., and Ali S., Eur. J. Med. Chem., 2009, vol. 44, pp. 2106–2112. https://doi.org/10.1016/j.ejmech.2008.10.012

    Article  CAS  PubMed  Google Scholar 

  9. Pintilie, O., Profire, L., Sunel, V., Popa, M., and Pui, A., Molecules, 2007, vol. 12, pp. 103–113. https://doi.org/10.3390/12010103

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Zamani, K., Faghifi, K., Tefighi, I., and Sharlatzadeh, R., Turk. J. Chem., 2004, vol. 28, pp. 95–100. https://doi.org/10.1086/423518

    Article  CAS  Google Scholar 

  11. Zan, X.I., Lai, L.H., Jin G.Y., and Zhong, Z.X., J. Agric. Food Chem., 2002, vol. 50, pp. 3757–3760. https://doi.org/10.1021/jf0201677

    Article  CAS  Google Scholar 

  12. Chem, H., Li, Z., and Han, Y., J. Agric. Food Chem., 2000, vol. 48, pp. 5312–5315. https://doi.org/10.1021/jf991065s

    Article  CAS  Google Scholar 

  13. Clerici, F., Pocar, D., Guido, M., Loche, A., Perlini, V., and Brufoni, M., J. Med. Chem, 2001, vol. 44, pp. 931–936. https://doi.org/10.1021/jm001027w

    Article  CAS  PubMed  Google Scholar 

  14. Sancak, K., Er, Y., and Unver, M., Turk. J. Chem., 2007, vol. 31, pp. 125–134.

    CAS  Google Scholar 

  15. Kurtzer, F.I., Katritzky, A.R., and Boulton, A., Adv. Heterocycl. Chem., 1965, vol. 5, p. 165.

    Google Scholar 

  16. Foroumadi, A., Mirzaei, M., and Shafiee, A., Farmaco, 2001, vol. 56, pp. 621–623. https://doi.org/10.1016/S0014-827X(01)01099-0

    Article  CAS  PubMed  Google Scholar 

  17. Awad, L.F., and El Ashry, E.S.H., Carbohydr. Res., 1983, vol. 122, pp. 69–79. https://doi.org/10.1016/0008-6215(83)88407-9

    Article  CAS  Google Scholar 

  18. Varvarasou, A., Sistra-Papastaikoud, T., Tsantili-Kakoulidou, A., and Vamvakides, A., Farmaco, 1998, vol. 53, pp. 320–326. https://doi.org/10.1016/S0014-827X(98)00024-X

    Article  Google Scholar 

  19. Holla, B.S., Poorjary, K.N., Rao, B.S., and Shivananda, M.K., Eur. J. Med. Chem., 2002, vol. 37, pp. 511–517. https://doi.org/10.1016/S0223-5234(02)01358-2

    Article  PubMed  Google Scholar 

  20. Glomb, T., Szymankiewicz, K., and Swiatek, P., Molecules, 2018, vol. 22, p. 3361. https://doi.org/10.3390/molecules23123361

    Article  CAS  Google Scholar 

  21. Flefel, E.M., Tantawy, W.A., El-Sayed, W.A., Sayed, H.H., and Fathy, N.M., J. Heterocycl. Chem., 2013, vol. 50, no. 2, pp. 344–350. https://doi.org/10.1002/jhet.1122

    Article  CAS  Google Scholar 

  22. El-Sayed, W.A., Ali, O.M., Hendy, H.A., and Abdel-Rahman, A.A.H., Chin. J. Chem., 2012, vol. 30, pp. 77–83. https://doi.org/10.1002/cjoc.201100029

    Article  CAS  Google Scholar 

  23. Zhang, S., Xu, Z., Gao, C., Ren, Q.C., Chang, L., Lv, Z.S., and Feng, L.S., Eur. J. Med. Chem., 2017, vol. 138, pp. 501–513. https://doi.org/10.1016/j.ejmech.2017.06.051

    Article  CAS  PubMed  Google Scholar 

  24. Jin, R.Y., Zeng, C.Y., Liang, X.H., Sun, X.H., Liu, Y.F., Wang, Y.Y., and Zhou, S., Bioorg. Chem., 2018, vol. 80, pp. 253–260. https://doi.org/10.1016/j.bioorg.2018.06.030

    Article  CAS  PubMed  Google Scholar 

  25. El-Essawy, F.A., El-Sayed, W.A., El-Kafrawy, S.A., Morshedy, A.S., and Abdel-Rahman, A.-H., Z. Naturforsch., 2008, vol. 63c, pp. 667–674. https://doi.org/10.1515/znc-2008-9-1010

    Article  Google Scholar 

  26. Mathew, V., Keshavayya, J., Vaidya, V.P., and Giles, D., Eur. J. Med. Chem., 2007, vol. 42, no. 6, pp. 823–840. https://doi.org/10.1016/j.ejmech.2006.12.010

    Article  CAS  PubMed  Google Scholar 

  27. El Shehry, M.F., Abu-Hashem, A.A., and El-Telbani, E.M., Eur. J. Med. Chem., 2010, vol. 45, pp. 1906–1911. https://doi.org/10.1016/j.ejmech.2010.01.030

    Article  CAS  PubMed  Google Scholar 

  28. Zhang, Q., Peng, Y., Wang, X.I., Keenan, S.M., Arora, S., and Welsh, W.J., J. Med. Chem., 2007, vol. 50, pp. 749–754. https://doi.org/10.1021/jm061142s

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Glomb, T., Szymankiewicz, K., and Świątek, P., Molecules, 2018, vol. 23, no. 12, p. 3361. https://doi.org/10.3390/molecules23123361

  30. El-Sayed, W.A., El-Sofany, W.I., Hussein, H.A., and Fathy, N.M., Nucleosides Nucleotides Nucleic Acids, 2017, vol. 36, no. 7, pp. 474–495. https://doi.org/10.1080/15257770.2017.1327665

  31. Fadda, A.A., Abdel-Rahman, A.H., El-Sayed, W.A., Zidan, T.A., and Badria, F.A., Chem. Heterocycl. Compd., 2011, vol. 47, no. 7, pp. 856–864. https://doi.org/10.1007/s10593-011-0847-4

  32. Kesagudu, D. and Chandrashekarachar, D., Indo Am. J. Pharm. Res., 2017, vol. 7, pp. 7541–7545. https://zenodo.org/record/2382131.

    Google Scholar 

  33. Alper-Hayta, S., Arisoy, M., Temiz-Arpaci, O., Yildiz, I., Aki, E., Ozkan, S., and Kaynak, F., Eur. J. Med. Chem., 2008, vol. 43, pp. 2568–2578. https://doi.org/10.1016/j.ejmech.2007.12.019

    Article  CAS  PubMed  Google Scholar 

  34. Kao, C.-L. and Chern, J.-W., Tetrahedron Lett., 2001, vol. 42, pp. 1111–1113. https://doi.org/10.1016/S0040-4039(00)02163-8

    Article  CAS  Google Scholar 

  35. El-Sayed, W.A., Ramiz, M.M.M., and Abdel-Rahman, A.A.-H., Monatsh. Chem., 2008, vol. 139, pp. 1499–1505. https://doi.org/10.1007/s00706-008-0941-1

    Article  CAS  Google Scholar 

  36. Rida, S.M., El-Hawash, S.A.M., Fahmy, H.T.Y., Hazzaa, A.A., and ElMeligy, M.M.M., Arch. Pharm. Res., 2006, vol. 29, pp. 826–833. https://doi.org/10.1007/BF02973901

    Article  CAS  PubMed  Google Scholar 

  37. El-Sayed, W.A., Abbas, H.-A.S., Mohamed, A.M., and Abdel-Rahman, A.A.-H., J. Heterocycl. Chem., 2001, vol. 48, pp. 1006–1013. https://doi.org/10.1002/jhet.679

    Article  CAS  Google Scholar 

  38. Romagnoli, R., Baraldi, P.G., Sarkar, T., Cara, C. L., Lopez, O.C., Carrion, M.D., Preti, D., Tolomeo, M., Balzarini, J., and Hamel, E., Med. Chem., 2008, vol. 4, pp. 558–564. https://doi.org/10.2174/157340608786242007

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Coşkun, D., Tekin, S., Sandal, S., and Coşkun, M. F., J. Chem., 2016, vol. 2016, pp. 1–8. https://doi.org/10.1155/2016/7678486

    Article  CAS  Google Scholar 

  40. 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

    Article  CAS  PubMed Central  Google Scholar 

  41. Mohamed, A.M., Al-Qalawi, H.R.M., El-Sayed, W.A., Arafa, W.A.A., Alhumaimess, M.S., and Hassan, A.K., Acta Pol. Pharm. Drug. Res., 2015, vol. 72, pp. 307–318.

    CAS  Google Scholar 

  42. El-Sayed, W.A., Khalaf, H.S., Mohamed, S.F., Hussien, H.A., Kutkat, O.M., and Amr, A.E., Russ. J. Gen. Chem., 2017, vol. 87, pp. 2444–2453. https://doi.org/10.1134/S1070363217100279

    Article  CAS  Google Scholar 

  43. El-Sayed, W.A., Abdel Megeid, R.E., and Abbas, H.S., Arch. Pharm. Res., 2011, vol. 34, no. 7, pp.1085–1096. https://doi.org/10.1007/s12272-011-0706-y

    Article  CAS  PubMed  Google Scholar 

  44. El-Sofanya, W.I., Othman, D.A.A., Mahrana, A.M., El-Manawaty, M.A., and El-Sayed, W.A., Russ. J. Bioorg. Chem., 2020, vol. 46, pp. 393–402. https://doi.org/10.1134/S106816202003005X

    Article  Google Scholar 

  45. Abu-Zaied, M.A., Nawwar, G.A., Swellem, R.H., and El-Sayed, S.H., Pharmacol. Pharm., 2012, vol. 3, no. 2, pp. 1–8. https://doi.org/10.4236/pp.2012.32034

    Article  CAS  Google Scholar 

  46. Kaur, R., Ranjan Dwivedi, A., Kumar, B., and Kumar, V., Anti-Cancer Agent ME, 2016, vol. 6, no. 4, pp. 465–489. https://doi.org/10.2174/1871520615666150819121106

  47. Kassem, A.F., Nassar, I.F., Abdel-Aal, M.T., Awad, H.M., and El-Sayed, W.A., Chem. Pharm. Bull., 2019, vol. 67, no. 8, pp. 888–895. https://doi.org/10.1248/cpb.c19-00280

    Article  CAS  Google Scholar 

  48. Tolan, H.E.M., Radwan, M.A.A., Khalaf, H.S., El-Bayaa, M.N., Awad, H.M., and El-Sayed, W.A., Russ. J. Gen. Chem., 2020, vol. 90, no. 8, pp. 1544–1552. https://doi.org/10.1134/S1070363220080241

  49. Nassar, I.F., El-Sayed, W.A., Ragab, T.I., Shalaby, A.S.G., and Mehany, A., Mini Rev. Med. Chem., 2019, vol. 19, no. 5, pp. 395–409. https://doi.org/10.2174/1389557518666180820125210

    Article  CAS  PubMed  Google Scholar 

  50. Khalaf, H.S., Tolan, H.E.M., El-Bayaa, M.N., Radwan, M.A.A., El-Manawaty, M., and El-Sayed, W.A., Russ. J. Gen. Chem., 2020, vol. 90, pp. 1706–1715. https://doi.org/10.1134/S1070363220090182

    Article  CAS  Google Scholar 

  51. Kassem, A.F., Abbas, E.M.H., El-Kady, D.S., Awad, H.M., and El-Sayed, W.A., Mini Rev. Med. Chem., 2019, vol. 19, no. 11, pp. 933–948. https://doi.org/10.2174/1389557519666181231121217

    Article  CAS  PubMed  Google Scholar 

  52. Ibrahim, Y.A., Carbohydr. Lett., 1996, vol. 1, pp. 425–432.

    CAS  Google Scholar 

  53. Hassan, A.S., Mady, M.F., Awad, H.M., and Hafez, T.S., Chin. Chem. Lett., 2017, vol. 28, pp. 388–393. https://doi.org/10.1016/j.cclet.2016.10.022

    Article  CAS  Google Scholar 

  54. Emam, A.N., Loutfy, S.A., Mostafa, A.A., Awad, H.M., and Mohamed, M.B., RSC Adv., 2017, vol. 7, pp. 23502–23514. https://doi.org/10.1039/C7RA01423F

    Article  CAS  Google Scholar 

  55. Khattab, R.R., Alshamari, A.K., Hassan, A.A., Elganzory, H.H., El-Sayed, W.A., Awad, H.M., Nossier, E.S., and Hassan, N.A., J. Enzyme Inhib. Med. Chem., 2021, vol. 36, no. 1, pp. 504–516. https://doi.org/10.1080/14756366.2020.1871335

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Menofia University, 32511, Shebin El-Kom, Egypt

    M. T. Abdel-Aal, E. S. Sharshar & Abd El-Hamid A. A. Ismail

  2. Department of Chemistry, College of Science, Qassim University, 51452, Buraidah, Saudi Arabia

    H. H. Elganzory & W. A. El-Sayed

  3. Photochemistry Department, National Research Centre, 12622, Cairo, Dokki, Egypt

    M. N. El-Bayaa & W. A. El-Sayed

  4. Department of Tanning Materials and Leather Technology, National Research Centre, 12622, Giza, Dokki, Egypt

    H. M. Awad

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  1. M. T. Abdel-Aal
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  3. H. H. Elganzory
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Abdel-Aal, M.T., Sharshar, E.S., Elganzory, H.H. et al. Synthesis and Anticancer Activity of New 1,3,4-Thiadiazolyl-1,2,4-Triazolyl and 1,3,4-Oxadiazolyl Hybrids, Their Thioglycosides, and Acyclic Analogs. Russ J Bioorg Chem 47, 1324–1334 (2021). https://doi.org/10.1134/S1068162021060029

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