Skip to main content

Advertisement

SpringerLink
Log in

One-pot synthesis and evaluation of anticancer activity of polyhydroquinoline derivatives catalyzed by [Msim]Cl

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

Abstract

A green protocol for an effective synthesis of bioactive polyhydroquinoline derivatives was developed via condensation of substituted salicylaldehyde, dimedone, ethyl acetoacetate and ammonium acetate catalyzed by 3-methyl-1-sulfonic acid imidazolium chloride ([Msim]Cl) in excellent yield. All synthesized derivatives were evaluated for inhibition of cancer cells. The initial assays reveals that some of the synthesized derivatives show significantly satisfactory inhibition activities against human breast cancer cells (MCF7) compared with the control (Adriamycin), which might be developed as novel lead scaffold for potential anticancer agents.

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
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. J. Zhu, H. Bienaymé, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  2. A. Domling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  3. I. Ugi, Pure Appl. Chem. 73, 187 (2001)

    Article  CAS  Google Scholar 

  4. C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)

    Article  CAS  Google Scholar 

  5. Y. Nishiya, N. Kosaka, M. Uchii, S.A. Sugimoto, Calcif. Tissue Int. 70, 30 (2002)

    Article  CAS  Google Scholar 

  6. R. Van der Lee, M. Pfaffendorf, P.A. van Zwieten, J. Hypertens. 18, 1677 (2000)

    Article  Google Scholar 

  7. K. Sirisha, G. Achaiah, V.M. Reddy, Arch. Pharm. 343, 342 (2010)

    Article  CAS  Google Scholar 

  8. L. Bazargan, S. Fouladdel, A. Shafiee, M. Amini, S.M. Ghaffari, E. Azizi, Cell Biol. Toxicol. 24(2), 165 (2008)

    Article  CAS  Google Scholar 

  9. M.S. Al-said, M.S. Bashandy, S.I. Al-gasoumi, M.M. Ghorab, Eur. J. Med. Chem. 46, 137 (2011)

    Article  CAS  Google Scholar 

  10. S.M. Nkosi, K. Anand, S. Anandakumar, S. Singh, A.A. Chuturgoon, R.M. Gengan, J. Photochem. Photobiol. B Biol. 165, 266 (2016)

    Article  CAS  Google Scholar 

  11. S. Yasar, M. Corrada, R. Brookmeyer, C. Kawas, Neurobiol. Ag. 26, 157 (2005)

    Article  CAS  Google Scholar 

  12. J.L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Catal. A: Chem. 256, 309 (2006)

    Article  CAS  Google Scholar 

  13. J. Safaei-Ghomi, M.A. Ghasemzadeh, J. Nanostruct. 1, 243 (2012)

    Google Scholar 

  14. A. Debache, L. Chouguiat, R. Boulcina, B. Carbonib, Open Org. Chem. J. 6, 12 (2012)

    Article  CAS  Google Scholar 

  15. M. Maheswara, V. Siddaiah, G. Lakishmi, V. Damu, C.V. Rao, Arkivoc 2, 201 (2006)

    Google Scholar 

  16. M.M. Heravi, M. Zakeri, S. Pooremamy, H.A. Oskooie, Synth. Commun. 1, 113 (2011)

    Google Scholar 

  17. L.M. Wang, J. Sheng, L. Zhang, Tetrahedron 61, 1539 (2005)

    Article  CAS  Google Scholar 

  18. E. Mosaddegh, A. Hassankhani, Arab. J. Chem. 5, 315 (2012)

    Article  CAS  Google Scholar 

  19. M. Nasr-Esfahani, S.J. Hoseini, M. Montazerozohori, R. Mehrabi, H. Nasrabad, J. Mol. Catal. A: Chem. 382, 99 (2014)

    Article  CAS  Google Scholar 

  20. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran. Chem. Soc. 7, 646 (2010)

    Article  CAS  Google Scholar 

  21. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Org. Prep. Proced. Int. 42, 95 (2010)

    Article  CAS  Google Scholar 

  22. B. Pouramiri, E. Tavakolinejad Kermani, Sci. Iran. C 23(3), 1095 (2016)

    Google Scholar 

Download references

Acknowledgements

We are thankful to Dr. P. L. More, Principal, Dnyanopasak College, Parbhani, Dr. W. N. Jadhav, Head of Department and Dr. B. R. Chavan, Principal, Yogeshwari Mahavidyalaya, Ambajogai for providing necessary facilities for the research work. We are also thankful to the Tata Memorial Centre Advanced Centre for Treatment Research and Education in Cancer (ACTREC) Anti-Cancer Drug Screening Facility (ACDSF), Sector-22, Kharghar, Navi Mumbai for providing anticancer activity.

Author information

Authors and Affiliations

  1. Department of Chemistry, Dnyanopasak College, Parbhani, MS, 431401, India

    S. C. Jadhvar, H. M. Kasraliker, S. V. Goswami, A. V. Chakrawar & S. R. Bhusare

Authors
  1. S. C. Jadhvar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. M. Kasraliker
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Goswami
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Chakrawar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. R. Bhusare
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. R. Bhusare.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jadhvar, S.C., Kasraliker, H.M., Goswami, S.V. et al. One-pot synthesis and evaluation of anticancer activity of polyhydroquinoline derivatives catalyzed by [Msim]Cl. Res Chem Intermed 43, 7211–7221 (2017). https://doi.org/10.1007/s11164-017-3069-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-3069-2

Keywords

Search

Navigation