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Synthesis and Cytotoxic Activity of New 1,4-Dithiazolyl-5-oxopyrrole Derivatives, Their 1,2,4-Triazoles and Nucleoside Analogs

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Abstract

New 1,4-bithiazolyl-5-oxopyrrole derivatives have been synthesized via a multicomponent reaction (MCR) and their structures characterized. N1-Phenyl- and N1-amino-substituted 1,2,4-triazole derivatives linked with bithiazolyl-5-oxopyrrole system also have been synthesized. Glycosylation of the latter s-triazole compounds by acetylated glycosyl halides has led to the corresponding thioglycoside derivatives. Cytotoxic activity data of the synthesized compounds against colon (HCT-116) and breast (MCF-7) human cancer sells determined by the MTT assay indicate two 1,2,4-triazole thioglycosides as potentially active in comparison with doxorubicin against MCF-7 cancer.

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REFERENCES

  1. Silverman, R.B., The Organic Chemistry of Drug Design and Drug Action, London: Academic Press, 1992, p. 263.

  2. Franchetti, P., and Grifantini, M., Curr. Med. Chem., 1999, vol. 6, p. 599.

    CAS  PubMed  Google Scholar 

  3. Matsuya, Y., Kawaguchi, T., Ishihara, K., Ahmed, K., Zhao, Q.L., Kondo, T., and Nemoto, H., Org. Lett., 2006, vol. 8, p. 4609. https://doi.org/10.1021/ol061922v

    Article  CAS  PubMed  Google Scholar 

  4. Srivastava, P.C., Pickering, M.V., Allen, L.B., Streeter, D.G., Campbell, M.T., Witkowski, J.T., Sidwell, R.W., and Robins, R.K., and J. Med. Chem., 1977, vol. 20, p. 256. https://doi.org/10.1021/jm00212a014

    Article  CAS  PubMed  Google Scholar 

  5. Merino, P., Tejero, T., Unzurrunzaga, F.J., Franco, S., Chiacchio, U., Saita, M.G., Iannazzo, D., Pipernoc, A., and Romeo, G., Tetrahedron: Asym., 2005, vol. 16, p. 3865. https://doi.org/10.1016/j.tetasy.2005.11.004

    Article  CAS  Google Scholar 

  6. Popsavin, M., Spaic, S., Svircev, M., Kojic, V., Bogdanovic, G., and Popsavina, V., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5317. https://doi.org/10.1016/j.bmcl.2006.07.086

  7. Popsavin, M., Spaic, S., Svircev, M., Kojic, V., Bogdanovic, G., and Popsavina, V., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 4123. https://doi.org/10.1016/j.bmcl.2007.05.050

  8. Lesyk, R., Vladzimirska, O., Holota, S., Zaprutko, L., and Gzella, A., Eur. J. Med. Chem., 2007, vol. 42, p. 641. https://doi.org/10.1016/j.ejmech.2006.12.006

    Article  CAS  PubMed  Google Scholar 

  9. Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Zaprutko, L., Gzella, A., and Lesyk, R., Eur. J. Med. Chem., 2009, vol. 44, p. 1396. https://doi.org/10.1016/j.ejmech.2008.09.032

    Article  CAS  PubMed  Google Scholar 

  10. Kaminskyy, D., Zimenkovsky, B., and Lesyk, R., Eur. J. Med. Chem., 2009, vol. 44, p. 3627. https://doi.org/10.1016/j.ejmech.2009.02.023

    Article  CAS  PubMed  Google Scholar 

  11. Williams, I.S., Joshi, P., Gatchie, L., Sharma, M., Satti, N.K., Vishwakarma, R.A., Chaudhuri, B., and Bharate, S.B., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 3683. https://doi.org/10.1016/j.bmcl.2017.07.010

    Article  CAS  PubMed  Google Scholar 

  12. Moreno, J.S., Agas, D., Sabbieti, M.G., Magno, M.D., Migliorini, A., and Loreto, M.A., Eur. J. Med. Chem., 2012, vol. 57, p. 391. https://doi.org/10.1016/j.ejmech.2012.09.008

    Article  CAS  Google Scholar 

  13. Dyson, L., Wright, A.D., Young, K.A., Sakoff, J.A., and McCluskey, A., Bioorg. Med. Chem., 2014, vol. 22, p. 1690. https://doi.org/10.1016/j.bmc.2014.01.021

  14. El Nezhawy, A., Gaballah, S., and Radwan, M.A., Tetrahedron Lett., 2009, vol. 50, p. 6646. https://doi.org/10.1016/j.tetlet.2009.09.068

  15. El Nezhawy, A., Radwan, M.A., and Gaballah, S., Arkivoc, 2009, vol. 12, p. 119. https://doi.org/10.3998/ark.5550190.0010.c10

  16. Radwan, M.A. and Abbas, E., Monatshefte fur Chemie, 2009, vol. 140, p. 229. https://doi.org/10.1007/s00706-008-0061-y

  17. Ghorab, M., Radwan, M.A., Taha, N., Amin, N., Shehab, M., and Faker, I., Phosphorus, Sulfur Silicon Rel. Elem., 2008, vol. 183, p. 2906. https://doi.org/10.1080/10426500802505424

  18. Fakhr, I., Hamdy, N., Radwan, M.A., and Ahmed, Y., Egyptian J. Chem., 2004, vol. 47, p. 201.

  19. 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

    Article  CAS  PubMed  Google Scholar 

  20. El-Sayed, W.A., Khalaf, H.S., Mohamed, S.F., Hssien, H.A., Kutkat, O.M., and El-Galil, E.A., Russ. J. Gen. Chem., 2017, vol. 87, p. 2444. https://doi.org/10.1134/S1070363217100279

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed Central  Google Scholar 

  22. Khan, A.T., Ghosh, A., and Khan, Md.M., Tetrahedron Lett., 2012, vol. 53, p. 2622. https://doi.org/10.1016/j.tetlet.2012.03.046

    Article  CAS  Google Scholar 

  23. 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, p. 2444. https://doi.org/10.1134/S1070363217100279

    Article  CAS  Google Scholar 

  24. Mansour, A.K., Ibrahim, Y.A., and Khalil, N.S.A.M., Nucleosid. Nucleotid., 1999, vol. 18, p. 2256. https://doi.org/10.1080/07328319908044880

    Article  Google Scholar 

  25. Emam, A.N., Samah, A.L., Mostafa, A.A., Hanem, M.A., and Mohamed, M.B., RSC Adv., 2017, vol. 7, p. 23502. https://doi.org/10.1039/C7RA01423F

    Article  CAS  Google Scholar 

  26. Eman, M.F., Wael, A.E., Ashraf, M.M., Walaa, I.E., and Hanem, M. A., Molecules, 2017, vol. 22, p. 1. https://doi.org/10.3390/molecules22010170

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to the National Research Centre and Qassim university for the facilities provided.

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Authors and Affiliations

  1. Department of Photochemistry, National Research Centre, 12622, Cairo, Dokki, Egypt

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

  2. Applied Organic Chemistry Department, National Research Center, 12622, Cairo, Dokki, Egypt

    M. A. A. Radwan

  3. Department of Chemistry, College of Science, Qassim University, 51452, Buridah, Saudi Arabia

    M. A. A. Radwan & W. A. El-Sayed

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

    H. S. Khalaf

  5. Department of Tanning Materials and Leather Technology, National Research Centre, 12622, Cairo, Dokki, Egypt

    H. M. Awad

Authors
  1. H. E. M. Tolan
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  2. M. A. A. Radwan
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  3. H. S. Khalaf
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  4. M. N. El-Bayaa
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  5. H. M. Awad
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  6. W. A. El-Sayed
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Corresponding authors

Correspondence to H. E. M. Tolan or M. A. A. Radwan.

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Tolan, H.E.M., Radwan, M.A.A., Khalaf, H.S. et al. Synthesis and Cytotoxic Activity of New 1,4-Dithiazolyl-5-oxopyrrole Derivatives, Their 1,2,4-Triazoles and Nucleoside Analogs. Russ J Gen Chem 90, 1544–1552 (2020). https://doi.org/10.1134/S1070363220080241

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  • DOI: https://doi.org/10.1134/S1070363220080241

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