Skip to main content

Advertisement

SpringerLink
Log in

An efficient method for the synthesis of new derivatives of 2,4,6-triarylpyridines as cytotoxic agents

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

New series of 2,4,6-triarylpyridines derivatives 5a–f and 6a–d were designed, synthesized and evaluated for their cytotoxic activity against breast cancer cell lines. Three-component reaction between acetophenones, ammonium acetate and 4-methyl or 2-methylpyridine in the presence of iodine in DMSO lead to title 2,4,6-triarylpyridines. This method allows the simple preparation of the desired products using readily available reagents under mild reaction conditions in good yields. Synthesized compounds were investigated for their cytotoxic activities against MDA-MB-231, MCF-7 and T-47D cell lines. Most of the synthesized compounds showed remarkable cytotoxicity, comparable to standard drug etoposide.

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

Fig. 1
Fig. 2
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. G.D. Henry, Tetrahedron 60, 6043 (2004)

    Article  CAS  Google Scholar 

  2. M. Borthakur, M. Dutta, S. Gogoi, R.C. Boruah, Synlett 2008, 3125 (2008)

    Article  Google Scholar 

  3. I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, S. Wang, Bioorg. Med. Chem. Lett. 13, 513 (2003)

    Article  CAS  Google Scholar 

  4. A. Shrestha, S. Park, S. Shin, T.M. Kadayat, G. Bist, P. Katila, Y. Kwon, E.S. Lee, Bioorg. Chem. 79, 1 (2018)

    Article  CAS  Google Scholar 

  5. Y. Asanuma, H. Eguchi, H. Nishiyama, I. Tomita, S. Inagi, Org. Lett. 19, 1824 (2017)

    Article  CAS  Google Scholar 

  6. J. Marquet, M. Moreno-Manas, P. Pacheco, M. Prat, A.R. Katritzky, B. Brycki, Tetrahedron 46, 5333 (1990)

    Article  CAS  Google Scholar 

  7. R.A. Abramovitch, J.M. Beckert, P. Chinnasamy, H. Xiaohua, W. Pennington, A.R.V. Sanjivamurthy, Heterocycles 28, 623 (1989)

    Article  CAS  Google Scholar 

  8. A.R. Katritzky, J.M. Aurrecoechea, K.K. Quian, E. Anna, G.J. Palenik, Heterocycles 25, 387 (1987)

    Article  CAS  Google Scholar 

  9. R.M. Martin, R.G. Bergman, J.A. Ellman, J. Org. Chem. 77, 2501 (2012)

    Article  CAS  Google Scholar 

  10. J.M. Neely, T. Rovis, J. Am. Chem. Soc. 135, 66 (2013)

    Article  CAS  Google Scholar 

  11. J. Wu, W. Xu, Z.X. Yu, J. Wang, J. Am. Chem. Soc. 137, 9489 (2015)

    Article  CAS  Google Scholar 

  12. X. Zhang, Z. Wang, K. Xu, Y. Feng, W. Zhao, X. Xu, Y. Yan, W. Yi, Green Chem. 18, 2313 (2016)

    Article  CAS  Google Scholar 

  13. R.S. Rohokale, B. Koenig, D.D. Dhavale, J. Org. Chem. 81, 7121 (2016)

    Article  CAS  Google Scholar 

  14. R. Karkia, R.K.Y. Junb, T.M. Kadayat, S. Shin, T.B.T. Magar, G. Bist, A. Shrestha, Y. Na, Y. Kwon, E.S. Lee, Eur. J. Med. Chem. 113, 228 (2016)

    Article  Google Scholar 

  15. R. Karkia, C. Song, T.M. Kadayat, T.B.T. Magar, G. Bist, A. Shrestha, Y. Na, Y. Kwon, E.S. Lee, Bioorg. Med. Chem. 23, 3638 (2015)

    Article  Google Scholar 

  16. R. Karkia, C. Park, K.Y. Jun, J.G. Jee, J.H. Lee, P. Thapa, T.M. Kadayat, Y. Kwon, E.S. Lee, Eur. J. Med. Chem. 84, 555 (2014)

    Article  Google Scholar 

  17. F. Kröhnke, W. Zecher, J. Curtze, D. Drechsler, K. Pfleghar, K.E. Schnalke, W. Weis, Angew. Chem. Int. Ed. 1, 626 (1962)

    Article  Google Scholar 

  18. F. Kröhnke, Synthesis 1, 1 (1976)

    Article  Google Scholar 

  19. K.T. Potts, M.J. Cipullo, P. Ralli, G. Theodoridis, J. Am. Chem. Soc. 103, 3584 (1981)

    Article  CAS  Google Scholar 

  20. T. Kobayashi, H. Kakiuchi, H. Kato, Bull. Chem. Soc. Jpn 64, 392 (1991)

    Article  CAS  Google Scholar 

  21. F. Palacios, A.M.O. de Retana, J. Oyarzabal, Tetrahedron Lett. 37, 4577 (1996)

    Article  CAS  Google Scholar 

  22. G.W.V. Cave, C.L. Raston, Chem. Commun. 22, 2199 (2000)

    Article  Google Scholar 

  23. S. Tu, T. Li, F. Shi, F. Fang, S. Zhu, X. Wei, Z. Zong, Chem. Lett. 34, 732 (2005)

    Article  CAS  Google Scholar 

  24. J.C. Xiang, Y. Cheng, Z.X. Wang, J.T. Ma, M. Wang, B.C. Tang, Y.D. Wu, A.X. Wu, Org. Lett. 19, 2997 (2017)

    Article  CAS  Google Scholar 

  25. Z. Tashrifi, M. Mohammadi-khanaposhtani, M. Shafiee Ardestani, M. Safavi, K. Rad-Moghadam, M. Mehrdad, B. Larijani, M. Mahdavi, Lett. Drug Des. Discov. 6, 213 (2019)

    Google Scholar 

  26. F. Khalili, S. Akrami, M. Safavi, M. Mohammadi-Khanaposhtani, M. Saeedi, S.K. Ardestani, B. Larijani, A. Zonouzi, M.B. Tehrani, M. Mahdavi, Anti-Cancer Agents Med. Chem. 19, 265 (2019)

    Article  CAS  Google Scholar 

  27. M. Nikpassand, L. Zare Fekri, M. Nabatzadeh, Comb. Chem. High Throughput Screen. 20, 533 (2017)

    Article  CAS  Google Scholar 

  28. M. Nikpassand, L. Zare Fekri, S. Sanagou, Dye. Pigment. 136, 140 (2017)

    Article  CAS  Google Scholar 

  29. H. Taherkhorsand, M. Nikpassand, Comb. Chem. High Throughput Screen. 21, 65 (2018)

    Article  CAS  Google Scholar 

  30. M. Nikpassand, D. Pirdelzendeh, Dye. Pigment. 130, 314 (2016)

    Article  CAS  Google Scholar 

  31. M. Nikpassand, L. Zare Fekri, P. Farokhian, Ultrason. Sonochem. 28, 341 (2016)

    Article  CAS  Google Scholar 

  32. M. Nikpassand, L. Zare Fekri, L. Karimian, M. Rassa, Curr. Org. Synth. 12, 358 (2015)

    Article  CAS  Google Scholar 

  33. L. Zare Fekri, M. Nikpassand, S. Pourmirzajani, B. Aghazadeh, RSC Adv. 8, 22313 (2018)

    Article  Google Scholar 

  34. M. Mohammadi-Khanaposhtani, S. Rezaei, R. Khalifeh, S. Imanparast, M.A. Faramarzi, S. Bahadorikhalili, M. Safavi, F. Bandarian, E.N. Esfahani, M. Mahdavi, B. Larijani, Bioorg. Chem. 80, 288 (2018)

    Article  CAS  Google Scholar 

  35. M. Mohammadi-Khanaposhtani, K. Fahimi, E. Karimpour-Razkenari, M. Safavi, M. Mahdavi, M. Saeedi, T. Akbarzadeh, Lett. Drug Des. Discov. 16, 818 (2019)

    Article  CAS  Google Scholar 

  36. M. Mohammadi-Khanaposhtani, M. Safavi, R. Sabourian, M. Mahdavi, M. Pordeli, M. Saeedi, S.K. Ardestani, A. Foroumadi, A. Shafiee, T. Akbarzadeh, Mol. Divers. 19, 787 (2015)

    Article  CAS  Google Scholar 

  37. R. Karkia, C. Park, K.Y. Jun, J.G. Jee, J.H. Lee, P. Thapa, T.M. Kadayat, Y. Kwon, E.S. Lee, Euro. J. Med. Chem. 84, 555 (2014)

    Article  Google Scholar 

Download references

Acknowledgements

Financial support from the Research Council of Islamic Azad University of Rasht branch is sincerely acknowledged.

Author information

Authors and Affiliations

  1. Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran

    Bahram Ahmadi Baloutaki, Mohammad Nikpassand & Hassan Kefayati

  2. Department of Chemistry, Payame Noor University (PNU), 19395-3697, Tehran, Iran

    Mohammad Hosein Sayahi

Authors
  1. Bahram Ahmadi Baloutaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Hosein Sayahi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohammad Nikpassand
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hassan Kefayati
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mohammad Hosein Sayahi or Mohammad Nikpassand.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baloutaki, B.A., Sayahi, M.H., Nikpassand, M. et al. An efficient method for the synthesis of new derivatives of 2,4,6-triarylpyridines as cytotoxic agents. Res Chem Intermed 46, 1153–1163 (2020). https://doi.org/10.1007/s11164-019-04025-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-04025-6

Keywords

Search

Navigation