Journal of the Iranian Chemical Society

, Volume 14, Issue 2, pp 387–394 | Cite as

Synthesis, structural elucidation and biological activities of organotin(IV) derivatives of 4-(2-thienyl)butyric acid

  • Farzana Shaheen
  • Muhammad Sirajuddin
  • Saqib Ali
  • Paul Joseph Dyson
  • Ali Haider
  • Muhammad Nawaz Tahir
  • Khadija Shahid
Original Paper
First Online:
Received:
Accepted:

Abstract

A series of tri- and diorganotin(IV) derivatives of 4-(2-thienyl)butyric acid have been synthesized by the reaction of ligand acid with tri- and diorganotin salts in 1:1 and 2:1 molar ratios, respectively. The synthesized compounds have been confirmed by CHNS elemental analyses, FTIR, multinuclear NMR (1H and 13C) spectroscopy and X-ray diffraction studies. NMR data reveal a 5-coordinate geometry for the triorganotin(IV) derivatives, while 6-coordinate for the diorganotin(IV) derivatives, respectively. The X-ray crystallographic analysis of the compound 2 showed polymeric 5-coordinate trigonal bipyramidal geometry. Antimicrobial studies were also evaluated against different strains of bacteria (Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis and Staphylococcus aureus) and fungi (Mucor species, Aspergillus solani, Helminthosporium oryzae, Aspergillus flavus, Aspergillus niger) to establish the biological significance of these compounds. The synthesized compounds probably work by interfering with the ability of bacteria to form cell walls by keeping unwanted substances from entering their cells and stop the contents of their cells from leaking out due which the bacteria get die. The antifungal activity of some of the tested compound is comparable to that of the standard drug, terbinafine. From their antimicrobial results, it was concluded that they might be used as potential candidate for the generation of new antimicrobial drugs.

Keywords

Organotin(IV) derivative NMR spectroscopy Single-crystal X-ray Antimicrobial activity 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgments

The authors are thankful to higher education commission of Pakistan for financial support during the present study.

References

  1. 1.
    Y.-F. Win, S.-G. Teoh, M. Vikneswaran, S.-T. Ha, P. Ibrahim, Int. J. Phys. Sci. 5, 1263 (2010)Google Scholar
  2. 2.
    S. Shahzadi, K. Shahid, S. Ali, Russ. J. Coord. Chem. 33, 403 (2007)CrossRefGoogle Scholar
  3. 3.
    N.F. Cardarelli, in Tin as a Vital Nutrient: Implications in Cancer Prophylaxis and Other Physiological Processes. Tin and Cell Malignancy Symposium, Chapman Lake, PA (USA), 27–29 May 1984 (CRC Press, Boca Raton, FL, 1986)Google Scholar
  4. 4.
    I. Haiduc, C. Silvestru, Coord. Chem. Rev. 99, 253 (1990)CrossRefGoogle Scholar
  5. 5.
    K. Khaled, N. Abdel-Shafi, N. Al-Mobarak, Int. J. Electrochem. Sci. 7, 1027 (2012)Google Scholar
  6. 6.
    M. Martin-Smith, S. Reid, J. Med. Chem. 1, 507 (1958)CrossRefGoogle Scholar
  7. 7.
    C.D. Badiceanu, A. Missir, C. Draghici, C. Larion, Farmacia 57, 771 (2009)Google Scholar
  8. 8.
    C.D. Bădiceanu, A.-V. Missir, Rev. Roum. Chim. 54, 27 (2009)Google Scholar
  9. 9.
    S. Abbas, M. Hussain, S. Ali, M. Parvez, A. Raza, A. Haider, J. Iqbal, J. Organomet. Chem. 724, 255 (2013)CrossRefGoogle Scholar
  10. 10.
    A.U. Rahman, M.I. Choudhary, W.J. Thomsen, Bioassay Techniques for Drug Development (Harwood Academic Publishers, The Netherlands, 2001)CrossRefGoogle Scholar
  11. 11.
    H.D. Yin, S.C. Xue, Appl. Organomet. Chem. 20, 283 (2006)CrossRefGoogle Scholar
  12. 12.
    M. Choudhary, M. Mazhar, S. Ali, X. Song, G. Eng, Metal Based Drugs 8, 275 (2001)CrossRefGoogle Scholar
  13. 13.
    N. Awang, I. Baba, M. Yousof, N.S. Akmal, N.F. Kamaludin, Am. J. Appl. Sci. 7, 1047 (2010)CrossRefGoogle Scholar
  14. 14.
    M. Sirajuddin, S. Ali, V. McKee, S. Zaib, J. Iqbal, RSC Adv. 4, 57505 (2014)CrossRefGoogle Scholar
  15. 15.
    M. Sirajuddin, S. Ali, V. McKee, M. Sohail, H. Pasha, Eur. J. Med. Chem. 84, 343 (2014)CrossRefGoogle Scholar
  16. 16.
    T.P. Lockhart, W.F. Manders, E.M. Holt, J. Am. Chem. Soc. 108, 6611 (1986)CrossRefGoogle Scholar
  17. 17.
    T.P. Lockhart, W.F. Manders, Inorg. Chem. 25, 892 (1986)CrossRefGoogle Scholar
  18. 18.
    R. Willem, A. Bouhdid, B. Mahieu, L. Ghys, M. Biesemans, E.R. Tiekink, D. de Vos, M. Gielen, J. Organomet. Chem. 531, 151 (1997)CrossRefGoogle Scholar
  19. 19.
    S. Niu, G.M. Li, R.A. Zingaro, J.H. Reibenspies, T. Ichiye, Heteroatom Chem. 13, 380 (2002)CrossRefGoogle Scholar
  20. 20.
    M. Sirajuddin, S. Ali, A. Haider, N.A. Shah, A. Shah, M.R. Khan, Polyhedron 40, 19 (2012)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2016

Authors and Affiliations

  • Farzana Shaheen
    • 1
  • Muhammad Sirajuddin
    • 2
  • Saqib Ali
    • 3
  • Paul Joseph Dyson
    • 4
  • Ali Haider
    • 3
  • Muhammad Nawaz Tahir
    • 5
  • Khadija Shahid
    • 6
  1. 1.Allama Iqbal Open University IslamabadIslamabadPakistan
  2. 2.Department of ChemistryUniversity of Science and Technology BannuBannuPakistan
  3. 3.Department of ChemistryQuaid-i-Azam University IslamabadIslamabadPakistan
  4. 4.Ecole Polytechnique Fédérale de Lausanne Institut Des Sciences et Ingénierie Chimiques EPFL SB ISIC LCOM, BCH 2402 (Batochime)LausanneSwitzerland
  5. 5.Department of PhysicsUniversity of SargodhaSargodhaPakistan
  6. 6.Department of Pharmaceutical Chemistry, Riphah Institute of Pharmaceutical SciencesRiphah International UniversityIslamabadPakistan

Personalised recommendations