Skip to main content
SpringerLink
Log in

Synthesis of New 6-[4-(2-Fluorophenylpiperazine-1-YL)]-3(2H)-Pyridazinone-2-Acethyl-2- (Substitutedbenzal)Hydrazone Derivatives and Evulation of Their Cytotoxic Effects in Liver and Colon Cancer Cell Lines

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

In this study, seven new 3(2H)-pyridazinone derivatives expected to show cytotoxic activity in liver and colon cancer cell lines were synthesized. Their structures were confirmed by the IR, 1H-NMR, 13C-NMR spectra and elementary analyses. Compunds V1-V7 were tested on HEP3B (liver cancer) and HTC116 (colon cancer) cell lines for cytotoxicity by using MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)- 2H-tetrazolium] proliferation assay. Human fibroblast cells were used as safety control in these tests. 6-[4-(2-Fluorophenyl)piperazine-1-yl]-3(2H)-pyridazinone-2-acetyl-2-(2-chlorobenzal)hydrazone (compound V3 ) was the most active agent with respect to HEP3B and HTC116 cell lines.

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

Scheme 1.
Fig. 1.

Similar content being viewed by others

Abbreviations

HEP3B:

liver cancer cell line

HTC116:

colon cancer cell line

MTS:

[3-(4,5-dimethylthi-azol-2-yl)- 5-(3-carboxymethoxyphenyl)-2-(4sulfophenyl)-2H-tetrazolium]

IC50:

half maximum inhibitory concentration

HF:

human fibroblast cell line

SHSY5Y:

neuroblastoma cell line

TLC:

thin layer chromatography

ATR:

attenuated total reflection

MM:

molecular mass

MP:

melting point

References

  1. J. Ferlay, I. Soerjomataram, R. Dikshit, et al., Int. J. Cancer, 136(5), 359–386 (2015).

    Article  Google Scholar 

  2. N. Howlader, A. M. Noone, M. Krapcho, et al. (eds.), SEER Cancer Statistics Review 1975 – 2014, National Cancer Institute, Bethesda, MD (2017); https: // seer.cancer.gov/csr /1975 2014/.

  3. R. Khoogar, B. C. Kim, J. Morris, and M. J. Wargovich, Am. J. Physiol. Gastrointest. Liver Physiol, 310(9), 629 – 644 (2016).

    Article  Google Scholar 

  4. S. M. S. Islam, T. D. Purnat, N. T. A. Phuong, et al., Globalization and Public Health Symp. (March 22, 2014, Munich, Germany) 10:81.

  5. F. A. Sloan and H. Gelband, Cancer Control Opportunities in Low- and Middle-Income Countries, National Academies Press, Washington, DC (2007).

    Google Scholar 

  6. X. Ma and H. Yu, Yale J. Biol. Med., 79(3 – 4), 85–94 (2006).

    PubMed  Google Scholar 

  7. A. G. Vaiopoulos, I. D. Kostakis, M. Koutsilieris, and A. G. Papavassiliou, Stem Cells, 30(3), 63–371 (2012).

    Article  Google Scholar 

  8. K. Bardhan and K. Liu, Cancer, 5(2), 676–713 (2013).

    Article  CAS  Google Scholar 

  9. R. N. Castle, A. Weissberger, and E. C. Taylor, The Chemistry of Heterocyclic Compounds, Vol. 28, John Wiley and Sons, New York (1973).

  10. E. Matrai, J. Mol. Struct., 408/409, 467 – 472 (1997).

  11. A. R. Katritzky and A. J. Boulton, Advances in Heterocyclic Chemistry, Vol. 9, Academic Press, New York – London (1968).

  12. A. A. Siddiqui, R. Mishra, and M. Shaharyar, Eur. J. Med. Chem., 45, 2283 – 2290 (2010).

    Article  CAS  Google Scholar 

  13. A. A. Siddiqui, R. Mishra, M. Shaharyar, et al, Bioorg. Med. Chem. Lett., 21, 1023 – 1026 (2011).

    Article  CAS  Google Scholar 

  14. S. Utku, M. Gökçe, G. Aslan, et al., Arzneim Forsch, 61, 1 – 7 (92011).

  15. C. Yamali, G. H. Ozan, B. Kahya, et al., Med. Chem. Res., 24, 1210 – 1217 (2015).

  16. P. Nagle, Y. Pawar, A. Sonawane, et al., Med. Chem. Res., 23, 918 – 926 (2014).

  17. M. F. Þahin, B. Badýçoðlu, M. Gökçe, et al., Arch. Pharm. Pharm. Med., 33, 445 – 452 (2004).

  18. I. G. Rathish, K. Javed, S. Ahmad, et al., Eur. J. Med. Chem., 49, 304 – 309 (2012).

    Article  CAS  Google Scholar 

  19. N. F. Abd El-Ghaffar, M. K. Mohamed, M. S. Kadah, J. Chem. Pharm. Res., 3, 248 – 259 (2011).

  20. M. Asif, Int. J. Adv. Chem., 2(2), 148 – 161 (2014).

    Article  Google Scholar 

  21. A. Bruel, C. Loge, M. L. Tauzia, et al., Eur. J. Med. Chem., 57, 225 – 233 (2012).

    Article  CAS  Google Scholar 

  22. Z. Özdemir,M. Gökçe, H. Uslu., et al., Intern. Multidisciplinary Symp. on Drug Research and Development (November 28 – 30, 2013, Antalya, Turkey).

  23. O. Çiftçi, Z. Özdemir, C. Acar, et al., Lett. Org. Chem., 15(4), 323 – 331 (2017).

    Article  Google Scholar 

  24. T. Önkol, M. Gökçe, İ. Orhan, and F. Kaynak, Org. Commun., 6, 55 – 67 (2013).

    Google Scholar 

  25. A. B. Özçelik, M. Gökçe, İ. Orhan, et al., Arzneim Forsch, 60(7), 452 – 458 (2010).

Download references

Conflict of Interests

No conflict of interests was reported by all authors.

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Inonu University, 44280, Malatya, Turkey

    Zeynep Özdemir

  2. Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Inonu University, 44280, Malatya, Turkey

    Neşe Başak-Türkmen

  3. Department of Medical Pharmacology, Faculty of Medicine, Yıldırım Beyazıt University, 06100, Ankara, Turkey

    İdris Ayhan

  4. Department of Medical Pharmacology, Faculty of Medicine, Pamukkale University, 20160, Denizli, Turkey

    Osman Çiftçi

  5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06100, Ankara, Turkey

    Mehtap Uysal

Authors
  1. Zeynep Özdemir
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Neşe Başak-Türkmen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. İdris Ayhan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Osman Çiftçi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mehtap Uysal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zeynep Özdemir.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Özdemir, Z., Başak-Türkmen, N., Ayhan, İ. et al. Synthesis of New 6-[4-(2-Fluorophenylpiperazine-1-YL)]-3(2H)-Pyridazinone-2-Acethyl-2- (Substitutedbenzal)Hydrazone Derivatives and Evulation of Their Cytotoxic Effects in Liver and Colon Cancer Cell Lines. Pharm Chem J 52, 923–929 (2019). https://doi.org/10.1007/s11094-019-01927-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-019-01927-y

Keywords

Search

Navigation