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Research on Chemical Intermediates

, Volume 42, Issue 2, pp 997–1015 | Cite as

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

  • Har Lal Singh
  • J. B. Singh
  • Sunita Bhanuka
Article

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.

Keywords

Amino acids Schiff base NMR spectroscopy Diorganotin(IV) complexes Theoretical calculations Antimicrobial activity 

Notes

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.

References

  1. 1.
    C. Andreini, I. Bertini, G. Cavallaro, G.L. Holliday, J.M. Thornton, J. Biol. Inorg. Chem. 13, 1205–1218 (2008)CrossRefGoogle Scholar
  2. 2.
    A.K. Cheetham, C.N.R. Rao, R.K. Feller, Chem. Commun. 46, 4780–4795 (2006)CrossRefGoogle Scholar
  3. 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)CrossRefGoogle Scholar
  4. 4.
    S.L.A. Kumar, M.S. Kumar, P.B. Sreeja, A. Sreekanth, Spectrochim. Acta Part A 113, 123–129 (2013)CrossRefGoogle Scholar
  5. 5.
    O.K. Farha, J.T. Hupp, Acc. Chem. Res. 43, 1166–1175 (2010)CrossRefGoogle Scholar
  6. 6.
    D.F. Weng, Z.M. Wang, S. Gao, Chem. Soc. Rev. 40, 3157–3181 (2011)CrossRefGoogle Scholar
  7. 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)CrossRefGoogle Scholar
  8. 8.
    P. Paul, P. Sengupta, S. Bhattacharya, J. Organomet. Chem. 724, 281–288 (2013)CrossRefGoogle Scholar
  9. 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)CrossRefGoogle Scholar
  10. 10.
    M. Nath, M. Vats, P. Roy, Eur. J. Med. Chem. 59, 310–321 (2013)CrossRefGoogle Scholar
  11. 11.
    F. Shaheen, A. Badshah, M. Gielen, G. Croce, U. Florke, U.D. de-Vos, S. Ali, J. Organomet. Chem. 695, 315–322 (2010)CrossRefGoogle Scholar
  12. 12.
    M.X. Li, L.Z. Zhang, M. Yang, J.Y. Niu, J. Zhou, Bioorg. Med. Chem. Lett. 22, 2418–2423 (2012)CrossRefGoogle Scholar
  13. 13.
    A. Karaküçük-İyidoğan, D. Taşdemir, E.E. Oruç-Emre, J. Balzarini, Eur. J. Med. Chem. 46, 5616–5624 (2011)CrossRefGoogle Scholar
  14. 14.
    V.B. Arion, M.A. Jakupec, M. Galanski, P. Unfried, B.K. Keppler, J. Inorg. Biochem. 91, 298–305 (2002)CrossRefGoogle Scholar
  15. 15.
    H.L. Singh, Spectrochim. Acta Part A 76, 253–258 (2010)CrossRefGoogle Scholar
  16. 16.
    H.L. Singh, Res. Chem. Intermed. 37, 1087–1101 (2011)CrossRefGoogle Scholar
  17. 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)CrossRefGoogle Scholar
  18. 18.
    D.K. Demertzi, M.A. Demertzis, J.R. Miller, C. Papadopoulou, C. Dodorou, G. Filousis, J. Inorg. Biochem. 86, 555–563 (2001)CrossRefGoogle Scholar
  19. 19.
    Y.F. Win, S.G. Teoh, T.S. Tengku-Muhammad, Y. Sivasothy, S.T. Ha, Am. J. Appl. Sci. 7, 301–308 (2010)CrossRefGoogle Scholar
  20. 20.
    J.S. Casas, M.S. Garcra-Tasende, J. Sordo, Coord. Chem. Rev. 209, 197–261 (2000)CrossRefGoogle Scholar
  21. 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)CrossRefGoogle Scholar
  22. 22.
    H.L. Singh, A.K. Varshney, Appl. Organomet. Chem. 15, 762–768 (2001)CrossRefGoogle Scholar
  23. 23.
    K.S. Prasad, L.S. Kumar, M. Prasad, H.D. Revanasiddappa, Bioinorg. Chem. Appl. (2010). doi: 10.1155/2010/854514 Google Scholar
  24. 24.
    K.E. Apple, Drug Metabol. Rev. 36, 763–786 (2004)CrossRefGoogle Scholar
  25. 25.
    M. Jain, S. Manju, R.V. Singh, Appl. Organomet. Chem. 18, 471–479 (2004)CrossRefGoogle Scholar
  26. 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)CrossRefGoogle Scholar
  27. 27.
    M.X. Li, D. Zhang, L.Z. Zhang, J.Y. Niu, B.S. Ji, J. Organomet. Chem. 696, 852–858 (2011)CrossRefGoogle Scholar
  28. 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)CrossRefGoogle Scholar
  29. 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)CrossRefGoogle Scholar
  30. 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)CrossRefGoogle Scholar
  31. 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)Google Scholar
  32. 32.
    H.L. Singh, J.B. Singh, K.P. Sharma, Res. Chem. Intermed. 38, 53–65 (2012)CrossRefGoogle Scholar
  33. 33.
    M. Das, S.E. Livingstone, Inorg. Chim. Acta 19, 5–10 (1976)CrossRefGoogle Scholar
  34. 34.
    B. Clarke, N. Clarke, D. Cunningham, T. Higgins, P. McArdle, M.N. Cholchuin, M. O’Gara, J. Organomet. Chem. 559, 56–64 (1998)Google Scholar
  35. 35.
    A.K. Saxena, J.K. Koacher, J.P. Tandon, Inorg. Nucl. Chem. Lett. 17, 229–233 (1981)CrossRefGoogle Scholar
  36. 36.
    G.K. Sandhu, R. Gupta, S.S. Sandhu, R.V. Parish, K. Brown, J. Organomet. Chem. 279, 373–384 (1985)CrossRefGoogle Scholar
  37. 37.
    M.T.H. Tarafder, A.R. Khan, Polyhedron 10, 819–822 (1991)CrossRefGoogle Scholar
  38. 38.
    H.L. Singh, J.B. Singh, A. Mukharjee, Bioinorg. Chem. Appl. (2013). doi: 10.1155/2013/425832 Google Scholar
  39. 39.
    M. Nath, P.K. Saini, A. Kumar, J. Organomet. Chem. 695, 1353–1362 (2010)CrossRefGoogle Scholar
  40. 40.
    H.L. Singh, J.B. Singh, Nat. Sci. 4, 170–178 (2012)Google Scholar
  41. 41.
    T.P. Lockhart, W.F. Manders, J. Am. Chem. Soc. 109, 7015–7020 (1987)CrossRefGoogle Scholar
  42. 42.
    K.C. Molloy, P.C. Waterfield, J. Organomet. Chem. 424, 281–287 (1992)CrossRefGoogle Scholar
  43. 43.
    A. Saxena, J.P. Tandon, A.J. Crowe, Polyhedron 4, 1085–1089 (1985)CrossRefGoogle Scholar
  44. 44.
    A. Lycka, J. Holecek, S. Angelika, T. Ivan, J. Organomet. Chem. 409, 331–339 (1991)CrossRefGoogle Scholar
  45. 45.
    T. Zoller, L. Iovkova-Berends, T. Berends, C. Dietz, G. Bradtmoller, K. Jurkschat, Inorg. Chem. 50, 8645–8653 (2011)CrossRefGoogle Scholar
  46. 46.
    D.A. Atwood, J.A. Jegier, K.J. Martin, D. Rutherford, J. Organomet. Chem. 503, C4–C7 (1995)CrossRefGoogle Scholar
  47. 47.
    G.F. de Sousa, V.M. Deflon, E. Niquet, A. Abras, J. Braz. Chem. Soc. 12, 493–498 (2001)CrossRefGoogle Scholar
  48. 48.
    A.A. Al-Amiery, R.I. Al-Bayati, K.Y. Saour, M.F. Radi, Res. Chem. Intermed. 38, 745–759 (2012)CrossRefGoogle Scholar
  49. 49.
    T.D. Thangadurai, K. Natarajan, Transit. Met. Chem. 26, 500–504 (2001)CrossRefGoogle Scholar
  50. 50.
    I. Pal, F. Basuli, S. Bhattacharya, Proc. Indian Acad. Sci. Chem. Sci. 114, 255–268 (2002)CrossRefGoogle Scholar
  51. 51.
    Y. Anjaneyula, R.P. Rao, Synth. React. Inorg. Met. Org. Chem. 16, 257–272 (1986)CrossRefGoogle Scholar
  52. 52.
    Z.H. Chohan, A. Scozzafava, C.T. Supuran, J. Enzy. Inhib. Med. Chem. 18, 259–263 (2003)CrossRefGoogle Scholar
  53. 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. 54.
    N. Dharmaraj, P. Viswanathamurthi, K. Natarajan, Transit. Met. Chem. 26, 105–109 (2001)CrossRefGoogle Scholar
  55. 55.
    A. Saxena, J.P. Tandon, Polyhedron 2, 443–446 (1983)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  1. 1.Department of ChemistryMody University of Science and TechnologyLakshmangarh, SikarIndia

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