SpringerLink
Log in

Synthesis, spectroscopy and biological studies of triphenyltin(IV) derivatives with carboxylated Schiff bases

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Schiff bases (S1–S8) were prepared by the reaction of 4-aminophenylacetic acid/5-aminoisophthalic acid with benzaldehyde/acetophenone/benzophenone/anthraquinone in ethanol. The sodium salts (NaS1–NaS8) of the Schiff bases were reacted further with triphenyltin(IV) chloride in methanol for 4 h to produce the organotin derivatives (C1–C8). The structures of the synthesized products (S1–S8 and C1–C8) were verified by elemental analysis, FT-IR analysis, 1H NMR spectroscopy, and thermogravimetry. Elemental analysis (CHN) data agreed well with the chemical composition of compounds. FT-IR spectroscopy demonstrated the isobidentate coordination mode of the carboxylate moiety and a trigonal bipyramidal geometry of Sn(IV) in the solid state of complexes. Proton NMR spectra displayed the signals of the Schiff base skeleton as well as the triphenyltin(IV) moieties in the complexes C1–C8 in their anticipated regions. The thermogravimetric analysis has shown a good agreement between the observed percentages of the evolved contents and residues and the theoretically calculated values. The Schiff bases have shown higher thermal stabilities as compared to their organotin(IV) derivatives, owing to stronger hydrogen bonding in the former case. The complexes exhibited higher antibacterial potential as compared to their free ligand precursors against the tested bacteria (Bacillus subtilis and Escherichia coli). The biological activities were dependent upon the structures of investigated products, nature of incorporated ligand and type (gram-positive or gram-negative) of the bacterial strains. The compounds were also tested for their in vitro hemolytic effects on human red blood cells while using PBS as a negative control (0% lysis) and triton X-100 as a positive control (100% lysis). Cytotoxicity values lie in the range of 1.5–7.9%, which is an acceptable range and renders the safe medicinal uses of all the synthesized products.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1.
Fig. 2.
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. A.M. Asiri, S.A. Khan, Molecules 15, 6850 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. G. Bagihalli, S. Patil, P. Badami, J. Iran. Chem. Soc. 6, 259 (2009)

    Article  CAS  Google Scholar 

  3. O. Bekircan, H. Bektas, Molecules 13, 2126 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. M. Diab, G.G. Mohamed, W. Mahmoud, A. El-Sonbati, S.M. Morgan, S. Abbas, Appl. Organomet. Chem. 33, e4945 (2019)

    Google Scholar 

  5. Z. Yang, P. Sun, Molbank 2006, M514 (2006)

    Article  Google Scholar 

  6. M. Zarei, A. Jarrahpour, Iran. J. Sci. Technol. Trans. A Sci. A3, 235 (2011)

    Google Scholar 

  7. H. Kargar, A. Adabi Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, J. Iran. Chem. Soc. 18, 2493 (2021)

    Article  CAS  Google Scholar 

  8. H. Kargar, M. Ashfaq, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M.N. Tahir, Inorg. Chim. Acta 536, 120878 (2022)

    Article  CAS  Google Scholar 

  9. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, M. Bahadori, M. Moghadam, M. Ashfaq, K.S. Munawar, M.N. Tahir, Polyhedron 213, 115622 (2022)

    Article  CAS  Google Scholar 

  10. S. Shujah, N. Muhammad, A. Shah, S. Ali, A. Meetsma, Z. Hussain, J. Organomet. Chem. 759, 19 (2014)

    Article  CAS  Google Scholar 

  11. N. Dharmaraj, P. Viswanathamurthi, K. Natarajan, Transit. Met. Chem. 26, 105 (2001)

    Article  CAS  Google Scholar 

  12. V. Mirkhani, S. Tangestaninejad, M. Moghadam, I. Mohammadpoor-Baltork, H. Kargar, J. Mol. Catal. A Chem. 242, 251 (2005)

    Article  CAS  Google Scholar 

  13. A. Jamshidvand, M. Sahihi, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, H.A. Rudbari, H. Kargar, R. Keshavarzi, S. Gharaghani, J. Mol. Liq. 253, 61 (2018)

    Article  CAS  Google Scholar 

  14. A.A. Ardakani, H. Kargar, N. Feizi, M.N. Tahir, J. Iran. Chem. Soc. 15, 1495 (2018)

    Article  CAS  Google Scholar 

  15. X.-B. Yang, Q. Wang, Y. Huang, P.-H. Fu, J.-S. Zhang, R.-Q. Zeng, Inorg. Chem. Commun. 25, 55 (2012)

    Article  CAS  Google Scholar 

  16. A.R. Bendale, R. Bhatt, A. Nagar, A.G. Jadhav, G. Vidyasagar, Der Pharma Chem. 3, 34 (2011)

    CAS  Google Scholar 

  17. V. Barba, E. Vega, R. Luna, H. Höpfl, H.I. Beltrán, L.S. Zamudio-Rivera, J. Organomet. Chem. 692, 731 (2007)

    Article  CAS  Google Scholar 

  18. S. Hussain, S. Ali, S. Shahzadi, S.K. Sharma, K. Qanungo, I.H. Bukhari, J. Coord. Chem. 65, 278 (2012)

    Article  CAS  Google Scholar 

  19. S. Hussain, S. Ali, S. Shahzadi, C. Rizzoli, Phosphorus Sulfur Silicon Relat. Elem. 188, 812 (2013)

    Article  CAS  Google Scholar 

  20. D. Ghazi, Z. Rasheed, E. Yousif, J. Dev. 3, 4 (2018)

    Google Scholar 

  21. A.G. Davies, J. Chem. Res. 34, 181 (2010)

    Article  CAS  Google Scholar 

  22. S. Mariam, S. Hussain, S. Ali, S. Shahzadi, S. Ramzan, M. Shahid, Iran. J. Sci. Technol. Trans. A Sci. 42, 1277 (2018)

    Article  Google Scholar 

  23. S. Hussain, Z. Zahid, M. Shahid, M.A. Abid, Arab. J. Sci. Eng. 44, 6423 (2019)

    Article  CAS  Google Scholar 

  24. S. Hussain, LGUJLS 2, 124 (2018)

    Article  Google Scholar 

  25. M. Affan, B. Fasihuddin, Y. Liew, S. Foo, J. Ismail, J. Sci. Res. 1, 306 (2009)

    Article  CAS  Google Scholar 

  26. Y. Farina, H. Adil, A. Ahmed, A. Graisa, E. Yousif, Aust. J. Basic Appl. Sci. 3, 1670 (2009)

    CAS  Google Scholar 

  27. C. Pettinari, F. Marchetti, R. Pettinari, D. Martini, A. Drozdov, S. Troyanov, Inorg. Chim. Acta 325, 103 (2001)

    Article  CAS  Google Scholar 

  28. W.T. Piver, Environ. Health Perspect. 4, 61 (1973)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. M. Nath, P.K. Saini, Dalton Trans. 40, 7077 (2011)

    Article  CAS  PubMed  Google Scholar 

  30. K. Jamil, R. Wajid, M. Bakhtiar, M. Danish, J. Iran. Chem. Soc. 7, 495 (2010)

    Article  CAS  Google Scholar 

  31. Y.-X. Tan, Z.-J. Zhang, Y. Liu, J.-X. Yu, X.-M. Zhu, D.-Z. Kuang, W.-J. Jiang, J. Mol. Struct. 1149, 874 (2017)

    Article  CAS  Google Scholar 

  32. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Bahadori, M. Moghadam, Inorg. Chem. Res. 6, 76 (2022)

    Google Scholar 

  33. H. Kargar, A.A. Ardakani, M.N. Tahir, M. Ashfaq, K.S. Munawar, J. Mol. Struct. 1229, 129842 (2021)

    Article  CAS  Google Scholar 

  34. S. Hussain, S. Ali, S. Shahzadi, M. Shahid, Cogent Chem. 1, 1029038 (2015)

    Article  Google Scholar 

  35. T. Riaz, M.A. Abbasi, T. Shazadi, M. Shahid, Pak. J. Pharm. Sci. 32, 697 (2019)

    CAS  PubMed  Google Scholar 

  36. T. Shahzadi, M. Zaib, T. Riaz, S. Shehzadi, M.A. Abbasi, M. Shahid, Arab. J. Sci. Eng. 44, 6435 (2019)

    Article  CAS  Google Scholar 

  37. S. Hussain, S. Ali, S. Shahzadi, M.N. Tahir, M. Shahid, J. Coord. Chem. 68, 2369 (2015)

    Article  CAS  Google Scholar 

  38. R.K. Agarwal, L. Singh, D.K. Sharma, Bioinorg. Chem. Appl. 2006, 1–10 (2006)

    Google Scholar 

  39. S. Arulmurugan, H.P. Kavitha, B. Venkatraman, Rasayan J. Chem. 3, 385 (2010)

    Google Scholar 

  40. J. Devi, J. Yadav, N. Singh, Res. Chem. Intermed. 45, 3943 (2019)

    Article  CAS  Google Scholar 

  41. S. Esmaielzadeh, M. Mohammadi, Bull. Chem. Soc. Ethiop. 33, 77 (2019)

    Article  CAS  Google Scholar 

  42. G. Eng, X. Song, A. Zapata, A.C. de Dios, L. Casabianca, R.D. Pike, J. Organomet. Chem. 692, 1398 (2007)

    Article  CAS  Google Scholar 

  43. S.M. Morgan, M. Diab, A. El-Sonbati, Appl. Organomet. Chem. 32, e4305 (2018)

    Article  Google Scholar 

  44. S. Hussain, I.H. Bukhari, S. Ali, S. Shahzadi, M. Shahid, K.S. Munawar, J. Coord. Chem. 68, 662 (2015)

    Article  CAS  Google Scholar 

  45. H.M. Refaat, H.A. El-Badway, S.M. Morgan, J. Mol. Liq. 220, 802 (2016)

    Article  CAS  Google Scholar 

  46. S. Nozha, S.M. Morgan, S.A. Ahmed, M. El-Mogazy, M. Diab, A. El-Sonbati, M. Abou-Dobara, J. Mol. Liq. 1227, 129525 (2021)

    CAS  Google Scholar 

  47. S. Hussain, S. Ali, S. Shahzadi, M. Riaz, K. Nazir, M.N. Arshad, A.M. Asiri, Arab. J. Sci. Eng. 45, 4785 (2020)

    Article  CAS  Google Scholar 

  48. M. Singh, S. Singh, S. Prasad, I. Gambhir, Dig. J. Nanomater. Biostruct. 3, 115 (2008)

    Google Scholar 

  49. B.G. Tweedy, Phytopathology 55, 910 (1964)

    Google Scholar 

  50. S.S. Konstantinović, B.C. Radovanović, S.P. Sovilj, S. Stanojević, J. Serbian Chem. Soc. 73, 7 (2008)

    Article  Google Scholar 

  51. C. Pellerito, L. Nagy, L. Pellerito, A. Szorcsik, J. Organomet. Chem. 691, 1733 (2006)

    Article  CAS  Google Scholar 

  52. M. Carcelli, A. Fochi, P. Pelagatti, G. Pelizzi, U. Russo, J. Organomet. Chem. 626, 161 (2001)

    Article  CAS  Google Scholar 

  53. S. Shahzadi, K. Shahid, S. Ali, J. Coord. Chem. 60, 2637 (2007)

    Article  CAS  Google Scholar 

  54. N. Sharma, V. Kumar, M. Kumari, A. Pathania, S. Chaudhry, J. Coord. Chem. 63, 3498 (2010)

    Article  CAS  Google Scholar 

  55. A. Sahraei, H. Kargar, M. Hakimi, M.N. Tahir, J. Mol. Struct. 1149, 576 (2017)

    Article  CAS  Google Scholar 

  56. A. Sahraei, H. Kargar, M. Hakimi, M.N. Tahir, Transit. Met. Chem. 42, 483 (2017)

    Article  CAS  Google Scholar 

  57. H. Kargar, M. Fallah-Mehrjardi, M. Ashfaq, K.S. Munawar, M.N. Tahir, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, A. Adabi Ardakani, S. Sedighi-Khavidak, J. Coord. Chem. 74, 2720 (2021)

    Article  CAS  Google Scholar 

  58. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H.A. Rudbari, A.A. Ardakani, S. Sedighi-Khavidak, K.S. Munawar, M. Ashfaq, M.N. Tahir, Polyhedron 213, 115636 (2022)

    Article  CAS  Google Scholar 

  59. H. Kargar, F. Aghaei-Meybodi, R. Behjatmanesh-Ardakani, M.R. Elahifard, V. Torabi, M. Fallah-Mehrjardi, M.N. Tahir, M. Ashfaq, K.S. Munawar, J. Mol. Struct. 1230, 129908 (2021)

    Article  CAS  Google Scholar 

  60. H. Kargar, F. Aghaei-Meybodi, M.R. Elahifard, M.N. Tahir, M. Ashfaq, K.S. Munawar, J. Coord. Chem. 74, 1534 (2021)

    Article  CAS  Google Scholar 

  61. H. Kargar, A.A. Ardakani, M.N. Tahir, M. Ashfaq, K.S. Munawar, J. Mol. Struct. 1233, 130112 (2021)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the support of Lahore Garrison University, Lahore, Pakistan (practical) and University of Agricultural Faisalabad, Pakistan (for biological activity studies) for this study.

Author information

Authors and Affiliations

  1. Institute of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, 64200, Pakistan

    Shabbir Hussain, Muhammad Saqib & Rifat Jawaria

  2. Department of Chemistry, Lahore Garrison University, Lahore, Pakistan

    Rabia Kiran & Muhammad Waqas

  3. Department of Chemistry, Division of Science and Technology, University of Education, Lahore, 54770, Pakistan

    Muhammad Ahmad

  4. Department of Chemistry, University of Mianwali, Mianwali, 42200, Pakistan

    Khurram Shahzad Munawar

  5. Institute of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan

    Khurram Shahzad Munawar

  6. Department of Chemistry and Biochemistry, University of Agriculture, Faisalabad, Pakistan

    Muhammad Shahid

  7. Department of Chemistry, Forman Christian College (A Chartered University), Lahore, 54600, Pakistan

    Shazma Massey

  8. Department of Education, Sukkur IBA University, Sukkur, 65200, Pakistan

    Rabia Baby

Authors
  1. Shabbir Hussain
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rabia Kiran
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Muhammad Ahmad
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Muhammad Saqib
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Khurram Shahzad Munawar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Muhammad Shahid
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Muhammad Waqas
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Shazma Massey
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Rifat Jawaria
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Rabia Baby
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shabbir Hussain.

Ethics declarations

Conflict of interest

There is no conflict of interest between the authors.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1329 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hussain, S., Kiran, R., Ahmad, M. et al. Synthesis, spectroscopy and biological studies of triphenyltin(IV) derivatives with carboxylated Schiff bases. J IRAN CHEM SOC 20, 1191–1203 (2023). https://doi.org/10.1007/s13738-023-02746-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-023-02746-5

Keywords

Search

Navigation