Skip to main content
SpringerLink
Log in

Design and synthesis of some new biologically active amidoalkyl naphthols in the presence of sulfonic acid functionalized silica-coated Fe3O4 nanoparticles

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

Abstract

The novel functionalized silica-coated Fe3O4 nanoparticles, Fe3O4@SiO2-TETA-SO3H, were synthesized by stabilizing of sulfonic group on the surface of silica-coated Fe3O4 nanoparticles. The structure of these nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, thermal gravimetric analysis and vibrating sample magnetometer and energy dispersive X-ray spectroscopy. The activity of the Fe3O4@SiO2-TETA-SO3H nanoparticles as a catalyst was investigated for benign one-pot synthesis of some new amidoalkyl naphthols using fatty acids as bio-based resources. This reaction afforded the desired products within short reaction times, high yields and easy work-up procedure. This acidic catalyst could be recycled and reused for six runs without significant change in its activity. Furthermore, the biological activity of the synthesized fatty amidoalkyl naphthols was evaluated against Staphylococcus aureus (ATCC 25,923) and Escherichia coli (ATCC 25,922) bacteria.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 2
Scheme 3
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. L.M. de Espinosa, M.A. Meier, Eur. Polym. J. 47, 837 (2011)

    Article  Google Scholar 

  2. J.T. Derksen, F.P. Cuperus, P. Kolster, Prog. Org. Coat. 27, 45 (1996)

    Article  CAS  Google Scholar 

  3. A. Gandini, T.M. Lacerda, Prog. Polym. Sci. 48, 1 (2015)

    Article  CAS  Google Scholar 

  4. K. Arisawa, H. Mitsudome, K. Yoshida, S. Sugimoto, T. Ishikawa, Y. Fujiwara et al., Biochem. Biophys. Res. Commun. 480, 641 (2016)

    Article  CAS  Google Scholar 

  5. R. Beims, V. Botton, L. Ender, D. Scharf, E. Simionatto, H. Meier et al., Fuel 217, 175 (2018)

    Article  CAS  Google Scholar 

  6. S.K. Khare, A. Kumar, T.M. Kuo, Bioresour. Technol. 100, 1482 (2009)

    Article  CAS  Google Scholar 

  7. Y. Yu, M. Shen, Q. Song, J. Xie, Carbohydr. Polym. 183, 91 (2018)

    Article  CAS  Google Scholar 

  8. B.S. Chhikara, D. Mandal, K. Parang, Eur. J. Med. Chem. 45, 4601 (2010)

    Article  CAS  Google Scholar 

  9. V. Gududuru, E. Hurh, J. Sullivan, J.T. Dalton, D.D. Miller, Bioorg. Med. Chem. Lett. 15, 4010 (2005)

    Article  CAS  Google Scholar 

  10. V. Venepally, R.C.R. Jala, Eur. J. Med. Chem. 141, 113 (2017)

    Article  CAS  Google Scholar 

  11. C.D.R.M. D’Oca, T. Coelho, T.G. Marinho, C.R.L. Hack, R. da Costa Duarte, P.A. da Silva et al., Bioorg. Med. Chem. Lett. 20, 5255 (2010)

    Article  Google Scholar 

  12. R. da Costa Duarte, R. Ongaratto, L.A. Piovesan, V.R. de Lima, V. Soldi, A.A. Merlo et al., Tetrahedron Lett. 53, 2454 (2012)

    Article  Google Scholar 

  13. R.C. Cioc, E. Ruijter, R.V. Orru, Green Chem. 16, 2958 (2014)

    Article  CAS  Google Scholar 

  14. M.S. Patil, C.K. Khatri, G.U. Chaturbhuj, Monatsh. Chem. 149, 1453 (2018)

    Article  CAS  Google Scholar 

  15. R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, S. Esmati, A. Shahrisa, Res. Chem. Intermed. 43, 6845 (2017)

    Article  CAS  Google Scholar 

  16. K. Nikoofar, S.M. Dizgarani, P Natl A Sci. 89, 629 (2019)

    CAS  Google Scholar 

  17. A.V. Gutnov, V.T. Abaev, O.P. Demidov, Chem. Heterocycl. Compd. 55, 280 (2019)

    Article  CAS  Google Scholar 

  18. A. Olyaei, M. Sadeghpour, RSC Adv. 9, 18467 (2019)

    Article  CAS  Google Scholar 

  19. M. Ahmadi, L. Moradi, M. Sadeghzadeh, Monatsh. Chem. 150, 1111 (2019)

    Article  CAS  Google Scholar 

  20. A.R. Moosavi-Zare, H. Goudarziafshar, F. Nooraei, Appl. Organomet. Chem. 34, e5252 (2020)

    Article  CAS  Google Scholar 

  21. R. Kardooni, A.R. Kiasat, J Taiwan Inst Chem Eng. 87, 241 (2018)

    Article  CAS  Google Scholar 

  22. L.Z. Fekri, M. Nikpassand, S.N. Khakshoor, J. Organomet. Chem. 894, 18 (2019)

    Article  CAS  Google Scholar 

  23. A.R. Khosropour, M.M. Khodaei, H. Moghannian, Synlett 2005, 0955 (2005)

    Article  Google Scholar 

  24. H. Moghanian, S. Ebrahimi, J. Saudi Chem. Soc. 18, 165 (2014)

    Article  Google Scholar 

  25. H. Moghanian, A. Mobinikhaledi, A. Blackman, E. Sarough-Farahani, RSC Adv. 4, 28176 (2014)

    Article  CAS  Google Scholar 

  26. C.A. Montalbetti, V. Falque, Tetrahedron 61, 10827 (2005)

    Article  CAS  Google Scholar 

  27. A. Khalafi-Nezhad, B. Mokhtari, M.N.S. Rad, Tetrahedron Lett. 44, 7325 (2003)

    Article  CAS  Google Scholar 

  28. S. Sarkar, A. Jha, K. Chattopadhyay, Mater. Res. Bull. 66, 1 (2015)

    Article  CAS  Google Scholar 

  29. A. Mobinikhaledi, H. Moghanian, Z. Souri, Lett. Org. Chem. 11, 432 (2014)

    Article  CAS  Google Scholar 

  30. K. Can, M. Ozmen, M. Ersoz, Coll. Surf. B. 71, 154 (2009)

    Article  CAS  Google Scholar 

  31. W. Stöber, A. Fink, E. Bohn, J. Coll. Interface Sci. 26, 62 (1968)

    Article  Google Scholar 

  32. A. Sheikhmohammadi, M. Safari, A. Alinejad, A. Esrafili, H. Nourmoradi, E. Asgari, J. Environ. Chem. Eng. 7, 103315 (2019)

    Article  CAS  Google Scholar 

  33. H. Moghanian, M.A.B. Fard, A. Mobinikhaledi, N. Ahadi, Res. Chem. Intermed. 44, 4083 (2018)

    Article  CAS  Google Scholar 

  34. H. Rostami, L. Shiri, Chemistry. Select. 3, 13487 (2018)

    CAS  Google Scholar 

  35. L. Shiri, H. Narimani, M. Kazemi, Appl. Organomet. Chem. 32, e3927 (2018)

    Article  Google Scholar 

  36. M. Shakourian-Fard, A.H. Rezayan, S. Kheirjou, A. Bayat, M.M. Hashemi, Bull. Chem. Soc. Jpn. 87, 982 (2014)

    Article  CAS  Google Scholar 

  37. D. Azarifar, Y. Abbasi, M. Jaymand, M.A. Zolfigol, M. Ghaemi, O. Badalkhani, J. Organomet. Chem. 895, 55 (2019)

    Article  CAS  Google Scholar 

  38. N. Foroughifar, A. Mobinikhaledi, H. Moghanian, Synth. Commun. 40, 1812 (2010)

    Article  CAS  Google Scholar 

  39. A. Mobinikhaledi, N. Foroughifar, T. Mosleh, A. Hamta, Iran J. Pharm. Res. 13, 873 (2014)

    CAS  PubMed  PubMed Central  Google Scholar 

  40. M. Shahi, N. Foroughifar, A. Mobinikhaledi, Iran J. Pharm. Res. 14, 757 (2015)

    PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support from the Research Council of Arak University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Arak University, 38156‑88138, Arak, Iran

    Razieh Rahimizadeh & Akbar Mobinikhaledi

  2. Department of Chemistry, Dezful Branch, Islamic Azad University, Dezful, Iran

    Hassan Moghanian

  3. Department of Laboratory, Amiralmomenin Hospital, Arak University of Medical Sciences, Arak, Iran

    Seyedeh sara Kashaninejad

Authors
  1. Razieh Rahimizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Akbar Mobinikhaledi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hassan Moghanian
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Seyedeh sara Kashaninejad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Akbar Mobinikhaledi.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 1541 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rahimizadeh, R., Mobinikhaledi, A., Moghanian, H. et al. Design and synthesis of some new biologically active amidoalkyl naphthols in the presence of sulfonic acid functionalized silica-coated Fe3O4 nanoparticles. Res Chem Intermed 48, 607–627 (2022). https://doi.org/10.1007/s11164-021-04610-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04610-8

Keywords

Search

Navigation