Skip to main content
SpringerLink
Log in

Synthesis, spectroscopic characterization, biological screening, and theoretical studies of organotin(IV) complexes of semicarbazone and thiosemicarbazones derived from (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone

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

Abstract

New organotin(IV) complexes of (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone thiosemicarbazone [L1H2], (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone phenylthiosemicarbazone [L2H2], and (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone semicarbazone [L3H2] with formula [R2SnL] (where R = Bu and Me) have been synthesized. The ligands and their organotin(IV) complexes were characterized by elemental analyses, molar conductivity, molecular weight determination, electronic, Fourier-transform infrared, and 1H, 13C, and 119Sn nuclear magnetic resonance spectral studies. The ligands act as tridentate and coordinate with organotin(IV) atom through the thiolate sulfur, azomethine nitrogen, and phenoxide oxygen atoms. The low molar conductance values in dimethylformamide indicate that the metal complexes are nonelectrolytes. Theoretical calculation is provided in support of the structures. The in vitro antimicrobial activities have been evaluated against Klebsiella sp., Bacillus cereus, Staphylococcus sp., Escherichia coli, Rhizopus, Aspergillus, Alternaria, and Penicillium. The screening results show that the organotin(IV) complexes have better antibacterial activities and have potential as drugs. Furthermore, it has been shown that dibutyltin(IV) derivative exhibits significantly better activity than the other organotin(IV) derivatives.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. C. Andreini, I. Bertini, G. Cavallaro, G.L. Holliday, J.M. Thornton, J. Biol. Inorg. Chem. 13, 1205–1218 (2008)

    Article  CAS  Google Scholar 

  2. A.K. Cheetham, C.N.R. Rao, R.K. Feller, Chem. Commun. 46, 4780–4795 (2006)

    Article  Google Scholar 

  3. C. Rodrigues, A.A. Batista, J. Ellena, E.E. Castellano, D. Benítez, H. Cerecetto, M. González, L.R. Teixeira, H. Beraldo, Eur. J. Med. Chem. 45, 2847–2853 (2010)

    Article  CAS  Google Scholar 

  4. S.L.A. Kumar, M.S. Kumar, P.B. Sreeja, A. Sreekanth, Spectrochim. Acta Part A 113, 123–129 (2013)

    Article  Google Scholar 

  5. O.K. Farha, J.T. Hupp, Acc. Chem. Res. 43, 1166–1175 (2010)

    Article  CAS  Google Scholar 

  6. D.F. Weng, Z.M. Wang, S. Gao, Chem. Soc. Rev. 40, 3157–3181 (2011)

    Article  CAS  Google Scholar 

  7. J.Y. Lee, O.K. Farha, J. Roberts, K.A. Scheidt, S.T. Nguyen, J.T. Hupp, Chem. Soc. Rev. 38, 1450–1459 (2009)

    Article  CAS  Google Scholar 

  8. P. Paul, P. Sengupta, S. Bhattacharya, J. Organomet. Chem. 724, 281–288 (2013)

    Article  CAS  Google Scholar 

  9. P. Paul, S. Datta, S. Halder, R. Acharyya, F. Basuli, R.J. Butcher, S.M. Peng, G.H. Lee, A. Castineiras, M.G.B. Drew, S. Bhattacharya, J. Mol. Catal. A: Chem. 344, 62–73 (2011)

    Article  CAS  Google Scholar 

  10. M. Nath, M. Vats, P. Roy, Eur. J. Med. Chem. 59, 310–321 (2013)

    Article  CAS  Google Scholar 

  11. F. Shaheen, A. Badshah, M. Gielen, G. Croce, U. Florke, U.D. de-Vos, S. Ali, J. Organomet. Chem. 695, 315–322 (2010)

    Article  CAS  Google Scholar 

  12. M.X. Li, L.Z. Zhang, M. Yang, J.Y. Niu, J. Zhou, Bioorg. Med. Chem. Lett. 22, 2418–2423 (2012)

    Article  Google Scholar 

  13. A. Karaküçük-İyidoğan, D. Taşdemir, E.E. Oruç-Emre, J. Balzarini, Eur. J. Med. Chem. 46, 5616–5624 (2011)

    Article  Google Scholar 

  14. V.B. Arion, M.A. Jakupec, M. Galanski, P. Unfried, B.K. Keppler, J. Inorg. Biochem. 91, 298–305 (2002)

    Article  CAS  Google Scholar 

  15. H.L. Singh, Spectrochim. Acta Part A 76, 253–258 (2010)

    Article  Google Scholar 

  16. H.L. Singh, Res. Chem. Intermed. 37, 1087–1101 (2011)

    Article  CAS  Google Scholar 

  17. K.S.O. Ferraz, L. Ferandes, D. Carrilho, M.C.X. Pinto, M.D.F. Leite, E.M. Souza-Fagundes, N.L. Speziali, I.C. Mendes, H. Beraldo, Bioorg. Med. Chem. 17, 7138–7144 (2009)

    Article  CAS  Google Scholar 

  18. D.K. Demertzi, M.A. Demertzis, J.R. Miller, C. Papadopoulou, C. Dodorou, G. Filousis, J. Inorg. Biochem. 86, 555–563 (2001)

    Article  Google Scholar 

  19. Y.F. Win, S.G. Teoh, T.S. Tengku-Muhammad, Y. Sivasothy, S.T. Ha, Am. J. Appl. Sci. 7, 301–308 (2010)

    Article  CAS  Google Scholar 

  20. J.S. Casas, M.S. Garcra-Tasende, J. Sordo, Coord. Chem. Rev. 209, 197–261 (2000)

    Article  CAS  Google Scholar 

  21. J.S. Casas, M.C. Rodrίguez-Argüelles, U. Russo, A. Sánchez, J. Sordo, A. Vázquez-López, S. Pinelli, P. Lunghi, A. Bonati, J.S. Casas, R. Albertini, J. Inorg. Biochem. 69, 283–292 (1998)

    Article  CAS  Google Scholar 

  22. H.L. Singh, A.K. Varshney, Appl. Organomet. Chem. 15, 762–768 (2001)

    Article  CAS  Google Scholar 

  23. K.S. Prasad, L.S. Kumar, M. Prasad, H.D. Revanasiddappa, Bioinorg. Chem. Appl. (2010). doi:10.1155/2010/854514

    Google Scholar 

  24. K.E. Apple, Drug Metabol. Rev. 36, 763–786 (2004)

    Article  Google Scholar 

  25. M. Jain, S. Manju, R.V. Singh, Appl. Organomet. Chem. 18, 471–479 (2004)

    Article  CAS  Google Scholar 

  26. G.L. Parrilha, J.G. da Silva, L.E. Gouveia, A.K. Gasparoto, R.P. Dias, W.R. Rocha, D.A. Santos, N.L. Speziali, H. Beraldo, Eur. J. Med. Chem. 46, 1473–1482 (2011)

    Article  CAS  Google Scholar 

  27. M.X. Li, D. Zhang, L.Z. Zhang, J.Y. Niu, B.S. Ji, J. Organomet. Chem. 696, 852–858 (2011)

    Article  CAS  Google Scholar 

  28. I.C. Mendes, F.B. Costa, G.M. de Lima, J.D. Ardisson, I. Garcia-Santos, A. Castiñeiras, H. Beraldo, Polyhedron 28, 1179–1185 (2009)

    Article  CAS  Google Scholar 

  29. I.C. Mendes, J.P. Moreira, J.D. Ardisson, R.G. dos Santos, P.R.O. da Silva, I. Garcia, A. Castiñeiras, H. Beraldo, Eur. J. Med. Chem. 43, 1454–1461 (2008)

    Article  CAS  Google Scholar 

  30. A. Perez-Rebolledo, J.D. Ayala, G.M. de Lima, N. Marchini, G. Bombieri, C.L. Zani, E.M. Souza-Fagundes, H. Beraldo, Eur. J. Med. Chem. 40, 467–472 (2005)

    Article  CAS  Google Scholar 

  31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision C.01. (Gaussian, Inc., Wallingford CT, 2004)

  32. H.L. Singh, J.B. Singh, K.P. Sharma, Res. Chem. Intermed. 38, 53–65 (2012)

    Article  CAS  Google Scholar 

  33. M. Das, S.E. Livingstone, Inorg. Chim. Acta 19, 5–10 (1976)

    Article  CAS  Google Scholar 

  34. B. Clarke, N. Clarke, D. Cunningham, T. Higgins, P. McArdle, M.N. Cholchuin, M. O’Gara, J. Organomet. Chem. 559, 56–64 (1998)

  35. A.K. Saxena, J.K. Koacher, J.P. Tandon, Inorg. Nucl. Chem. Lett. 17, 229–233 (1981)

    Article  CAS  Google Scholar 

  36. G.K. Sandhu, R. Gupta, S.S. Sandhu, R.V. Parish, K. Brown, J. Organomet. Chem. 279, 373–384 (1985)

    Article  CAS  Google Scholar 

  37. M.T.H. Tarafder, A.R. Khan, Polyhedron 10, 819–822 (1991)

    Article  CAS  Google Scholar 

  38. H.L. Singh, J.B. Singh, A. Mukharjee, Bioinorg. Chem. Appl. (2013). doi:10.1155/2013/425832

    Google Scholar 

  39. M. Nath, P.K. Saini, A. Kumar, J. Organomet. Chem. 695, 1353–1362 (2010)

    Article  CAS  Google Scholar 

  40. H.L. Singh, J.B. Singh, Nat. Sci. 4, 170–178 (2012)

    Google Scholar 

  41. T.P. Lockhart, W.F. Manders, J. Am. Chem. Soc. 109, 7015–7020 (1987)

    Article  CAS  Google Scholar 

  42. K.C. Molloy, P.C. Waterfield, J. Organomet. Chem. 424, 281–287 (1992)

    Article  CAS  Google Scholar 

  43. A. Saxena, J.P. Tandon, A.J. Crowe, Polyhedron 4, 1085–1089 (1985)

    Article  CAS  Google Scholar 

  44. A. Lycka, J. Holecek, S. Angelika, T. Ivan, J. Organomet. Chem. 409, 331–339 (1991)

    Article  CAS  Google Scholar 

  45. T. Zoller, L. Iovkova-Berends, T. Berends, C. Dietz, G. Bradtmoller, K. Jurkschat, Inorg. Chem. 50, 8645–8653 (2011)

    Article  CAS  Google Scholar 

  46. D.A. Atwood, J.A. Jegier, K.J. Martin, D. Rutherford, J. Organomet. Chem. 503, C4–C7 (1995)

    Article  CAS  Google Scholar 

  47. G.F. de Sousa, V.M. Deflon, E. Niquet, A. Abras, J. Braz. Chem. Soc. 12, 493–498 (2001)

    Article  Google Scholar 

  48. A.A. Al-Amiery, R.I. Al-Bayati, K.Y. Saour, M.F. Radi, Res. Chem. Intermed. 38, 745–759 (2012)

    Article  CAS  Google Scholar 

  49. T.D. Thangadurai, K. Natarajan, Transit. Met. Chem. 26, 500–504 (2001)

    Article  CAS  Google Scholar 

  50. I. Pal, F. Basuli, S. Bhattacharya, Proc. Indian Acad. Sci. Chem. Sci. 114, 255–268 (2002)

    Article  CAS  Google Scholar 

  51. Y. Anjaneyula, R.P. Rao, Synth. React. Inorg. Met. Org. Chem. 16, 257–272 (1986)

    Article  Google Scholar 

  52. Z.H. Chohan, A. Scozzafava, C.T. Supuran, J. Enzy. Inhib. Med. Chem. 18, 259–263 (2003)

    Article  CAS  Google Scholar 

  53. K.S. Prasad, L.S. Kumar, S.C. Shekar, M. Prasad, H.D. Revanasiddappa, Chem. Sci. J. 12, 1–10 (2001)

    Google Scholar 

  54. N. Dharmaraj, P. Viswanathamurthi, K. Natarajan, Transit. Met. Chem. 26, 105–109 (2001)

    Article  CAS  Google Scholar 

  55. A. Saxena, J.P. Tandon, Polyhedron 2, 443–446 (1983)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the Dean of Faculty of Engineering and Technology, Mody University of Science and Technology, Lakshmangarh, Sikar, for providing facilities necessary to carry out this research work. They are also grateful to Dr. T. Dewa, Department of Microbiology, University of Delhi, for providing antimicrobial screening facilities. The authors are also grateful to Dr. Sangeeta Jhajharia for linguistic corrections.

Conflict of interest

The authors declare that they have no conflict of interest.

Author information

Authors and Affiliations

  1. Department of Chemistry, Mody University of Science and Technology, Lakshmangarh, Sikar, Rajasthan, India

    Har Lal Singh, J. B. Singh & Sunita Bhanuka

Authors
  1. Har Lal Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. B. Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sunita Bhanuka
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Har Lal Singh.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Singh, H.L., Singh, J.B. & Bhanuka, S. Synthesis, spectroscopic characterization, biological screening, and theoretical studies of organotin(IV) complexes of semicarbazone and thiosemicarbazones derived from (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone. Res Chem Intermed 42, 997–1015 (2016). https://doi.org/10.1007/s11164-015-2069-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2069-3

Keywords

Search

Navigation