Skip to main content
SpringerLink
Log in

Synthesis and anticancer activity of arylazothiazoles and 1,3,4-thiadiazoles using chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A novel series of 4-substituted 5-arylazo-2-[1-(pyrrol-3-yl)ethylidenehydrazinyl]thiazoles and 5-arylazo-2-[1-(pyrrol-3-yl)ethylidenehydrazinyl]-2,3-dihydrothiazol-3-amines was prepared by cyclocondensation of α-oxohydrazonoyl halides with 1-(pyrrol-3-yl)-ethylidenethiosemicarbazide and 1-(pyrrol-3-yl)ethylidenethiocarbohydrazide, respectively. These cyclocondensation reactions were achieved by using chitosan-grafted-poly(4-vinylpyridine) as a novel basic catalyst under microwave irradiation. Furthermore, the reaction of the above mentioned thiosemicarbazide and thiocarbohydrazide with N-phenylbenzenecarbohydrazonyl chlorides (bereft of the α-oxo group) using chitosan-grafted catalyst proceeded via a similar mechanism and afforded the same 2-hydrazono-1,3,4-thiadiazoles. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences as well as by their synthesis via alternative methods. Finally, the appraisal of the newly synthesized products for their anticancer activity against a colon carcinoma cell line (HCT-116) and liver carcinoma cell line (HEPG2-1) revealed promising activity, especially 4-phenyl- and 4-(thiophen-2-yl)-substituted 1,3-thiazole derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Scheme 5

Similar content being viewed by others

References

  1. Clark, J. H.; Macquarrie, D. J. Green Chemistry and Technology; Blackwell: Abingdon, 2002.

    Book  Google Scholar 

  2. Kunbeck, D.; Saidulu, G.; Reddy, K. R.; Diaz, D. Green Chem. 2012, 14, 378.

    Article  Google Scholar 

  3. Bommarius, A. S.; Riebel, B. R. Biocatalysis: Fundamentals and Applications; Wiley-VCH: Weinheim, 2004, p. 624.

    Book  Google Scholar 

  4. Qin, Y.; Zhao, W.; Yang, L.; Zhang, X.; Cui, Y. Chirality 2012, 24, 640.

    Article  CAS  Google Scholar 

  5. Watile, R. A.; Bhanage, B. M. Ind. J. Chem. 2012, 51A, 1354.

    CAS  Google Scholar 

  6. Al-Matar, H. M.; Khalil, K. D.; Meier, H.; Kolshorn, H.; Elnagdi, M. H. ARKIVOC 2008, (XVI), 288.

  7. Gomha, S. M.; Riyadh, S. M. ARKIVOC 2009, (XI), 58.

  8. Khalil, K. D.; Al-Matar, H. M.; Elnagdi, M. H. Eur. J. Chem. 2010, 1, 252.

    Article  CAS  Google Scholar 

  9. Guibal, E. Prog. Polym. Sci. 2005, 30, 71.

    Article  CAS  Google Scholar 

  10. Khalil, K. D.; Al-Matar, H. M. Molecules 2013, 18, 5288.

    Article  CAS  Google Scholar 

  11. Yen, M-S.; Chen, C-W. Dyes Pigments 2010, 86, 129.

    Article  CAS  Google Scholar 

  12. Maradiya, H. R. J. Saudi Chem. Soc. 2010, 14, 77.

    Article  CAS  Google Scholar 

  13. Zadafiya, S. K.; Tailor, J. H.; Malik, G. M. J. Chem. 2013, 2013, 1.

    Article  Google Scholar 

  14. Eberlin, M. N.; Kascheres, C. J. Org. Chem. 1988, 53, 2084.

    Article  CAS  Google Scholar 

  15. de Oliveira Cardoso, M. V.; de Siqueira, L. R. P.; de Silva, E. B.; Costa, L. B.; Hernandes, M. Z.; Rabello, M. M.; Ferreira, R. S.; de Cruz, L. F.; Moreira, D. R. M.; Pereira, V. R. A.; de Castro, M. C. A. B.; Bernhardt, P. V.; Leite, A. C. Eur. J. Med. Chem. 2014, 86, 48.

    Article  Google Scholar 

  16. Rostom, S. A. F.; Faidallah, H. M.; Radwan, M. F.; Badr, M. H. Eur. J. Med. Chem. 2014, 76, 170.

    Article  CAS  Google Scholar 

  17. Sayed, A. R. Tetrahedron 2012, 68, 2784.

    Article  CAS  Google Scholar 

  18. Hassan, A. A.; Mohamed, N. K.; Aly, A. A.; Mourad, A. F. E. Monatsh. Chem. 1997, 128, 61.

    Article  CAS  Google Scholar 

  19. Sayed, A. R. Tetrahedron Lett. 2010, 51, 4490.

    Article  CAS  Google Scholar 

  20. Hu, Y.; Li, C-Y.; Wang, X-M.; Yang, Y-H.; Zhu, H-L. Chem. Rev. 2014, 114, 5572.

    Article  CAS  Google Scholar 

  21. Wolkoff, P. Can. J. Chem. 1975, 53, 1333.

    Article  CAS  Google Scholar 

  22. Geies, A. A.; Kamal-Eldeen, A. M.; Abdelhafez, A. A.; Gaber, A. M. Phosphor, Sulfur Silicon Relat. Elem. 1991, 56, 87.

    Article  CAS  Google Scholar 

  23. Ranu, B. C.; Banerjee, S. Org. Lett. 2005, 7, 3049.

    Article  CAS  Google Scholar 

  24. Eweiss, N. F.; Osman, A. J. Heterocycl. Chem. 1980, 17, 1713.

    Article  CAS  Google Scholar 

  25. Shawali, A. S.; Abdelhamid, A. O. Bull. Chem. Soc. Jpn. 1976, 49, 321.

    Article  CAS  Google Scholar 

  26. Klančnik, A.; Piskernik, S. B.; Jeršek, B.; Možina, S. S. J. Microbiol. Methods 2010, 81, 121.

    Article  Google Scholar 

  27. Gangadevi, V.; Muthumary, J. Afr. J. Biotechnol. 2007, 6, 1382.

    CAS  Google Scholar 

  28. Mosmann, T. J. Immunol Methods 1983, 65, 55.

    Article  CAS  Google Scholar 

  29. Al-Salahi, R; Alswaidan, I.; Ghabbour, H. A.; Ezzeldin, E.; Elaasser, M.; Marzouk, M. Molecules 2015, 20, 5099.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt

    Sobhi M. Gomha & Sayed M. Riyadh

  2. Department of Chemistry, Faculty of Science, Taibah University, Almadinah, Almunawrah, 30002, Saudi Arabia

    Sayed M. Riyadh & Elmahdi A. Mahmmoud

  3. Regional Center for Mycology and Biotechnology, Al-Azhar University, Cairo, 11651, Egypt

    Mahmoud M. Elaasser

Authors
  1. Sobhi M. Gomha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sayed M. Riyadh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Elmahdi A. Mahmmoud
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mahmoud M. Elaasser
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sayed M. Riyadh.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(11/12), 1030–1038

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 1608 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gomha, S.M., Riyadh, S.M., Mahmmoud, E.A. et al. Synthesis and anticancer activity of arylazothiazoles and 1,3,4-thiadiazoles using chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst. Chem Heterocycl Comp 51, 1030–1038 (2015). https://doi.org/10.1007/s10593-016-1815-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1815-9

Keywords

Search

Navigation