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Synthesis, Spectroscopic Studies and Biological Applications of Organotin(IV) Derivatives of 3-[N-(4-Nitrophenyl)-amido]propenoic Acid and 3-[N-(4-Nitrophenyl)-amido]propanoic Acid

  • Shahid, Khadija (Department of Chemistry, Quaid-i-Azam University) ;
  • Shahzadi, Saira (Department of Chemistry, Quaid-i-Azam University) ;
  • Ali, Saqib (Department of Chemistry, Quaid-i-Azam University) ;
  • Mazhar, M. (Department of Chemistry, Quaid-i-Azam University)
  • Published : 2006.01.20

Abstract

New organotin(IV) derivatives with general formulae R_2SnL_2 and R_3SnL, where R = methyl, n-butyl, n-octyl and phenyl and HL is either 3-[N-(4-nitrophenyl)amido]-propenoic acid or 3-[N-(4-nitrophenyl)amido] propanoic acid have been synthesized in 1 : 2 and 1 : 1 molar ratio by different methods. The FTIR spectra clearly demonstrated that the organotin(IV) moieties react with [O,O] atoms of the ligands. The bonding and coordination behavior in these complexes are discussed on the basis of multinuclear (^1H,\,^{13}C,\,^{119}Sn) NMR and mass spectrometric studies. Antibacterial, and antifungal screening tests were performed for these compounds and reported here. These values were compared to those of the precursors and it was found that diorganotin(IV) complexes exhibit less activity as compared to triorganotin(IV) complexes . LD_{50} data were obtained by Brine Shrimp assay method. Insecticidal activity was performed for selective compounds by contact toxicity method.

Keywords

References

  1. Honnik, W. D.; Zuckerman, J. J. J. Organomet. Chem. 1979, 133, 178
  2. Harrison, P. G.; Philips, R. C. J. Organomet. Chem. 1979, 37, 182
  3. Molloy, K. C.; Purcell, T. G.; Schumann, H.; Zuckerman, J. J. Organometallics 1986, 5, 85 https://doi.org/10.1021/om00132a014
  4. Holecek, J.; Handlir, K.; Nadvornik, M.; Lycka, A. J. Organomet. Chem. 1983, 147, 258
  5. Ng, S. W.; Wai, C.; Kumar Das, V. G. J. Organomet. Chem. 1988, 59, 345
  6. Sandhu, G. K.; Verma, S. P.; Tieknik, E. R. T. J. Organomet. Chem. 1990, 195, 393
  7. Tieknik, E. R. T. Appl. Organomet. Chem. 1991, 5, 1 https://doi.org/10.1002/aoc.590050102
  8. Ng, S. W.; Kumar Das, V. G.; Tieknik, E. R. T. J. Organomet. Chem. 1991, 111, 403
  9. Vasta, C.; Jain, V. K.; Das, T. K.; Tieknik, E. R. T. J. Organomet. Chem. 1991, 21, 421
  10. Teoh, S. G.; Ang, S. H.; Looi, E. S.; Keok, C. A.; Teo, S. B.; Fun, H. K. J. Organomet. Chem. 1997, 527, 15 https://doi.org/10.1016/S0022-328X(96)06589-8
  11. Sexana, A. K.; Huber, F. Coord. Chem. Rev. 1989, 95, 109 https://doi.org/10.1016/0010-8545(89)80003-7
  12. Barbieri, R. Inorg. Chim. Acta 1992, 191, 253 https://doi.org/10.1016/S0020-1693(00)93468-6
  13. Gupta, S. P. Chem. Rev. 1994, 94, 1507 https://doi.org/10.1021/cr00030a003
  14. Gielen, M. Coord. Chem. Rev. 1996, 151, 41 https://doi.org/10.1016/S0010-8545(96)90193-9
  15. Vos, D. de; Willem, R.; Gielen, M.; Van Wingerden, K. C.; Nooter, K. Met. Based Drugs 1998, 5, 179 https://doi.org/10.1155/MBD.1998.179
  16. Holloway, C. E.; Melnik, M. Main Group Met. Chem 2000, 23, 555
  17. Tin-Based Antitumor Drugs; NATO ASI Series, H37: Gielen, M., Ed.; Springer-Verlag: Berlin, 1990
  18. Okawa, R.; Webster, D. E.; Rockow, E. R. J. Am. Chem. Soc. 1960, 82, 3287 https://doi.org/10.1021/ja01498a013
  19. Tiano, L.; Fedeli, D.; Moretti, M.; Falcioni, G. Appl. Organomet. Chem. 2001, 15, 575 https://doi.org/10.1002/aoc.207
  20. Gabbianelli, R.; Villarini, M.; Falcioni, G.; Lupidi, G. Appl. Organomet. Chem. 2002, 16, 163 https://doi.org/10.1002/aoc.275
  21. Gielen, M.; El-Khloufi, A.; Biesemans, M.; Willem, R.; Meunier- Piert, J. Polyhedron 1992, 11, 1861 https://doi.org/10.1016/S0277-5387(00)83733-X
  22. Gielen, M.; Lelieveled, P.; Vos, D. de; Pan, H.; Willem, R.; Biesemans, M.; Fiebig, H. H. Inorg. Chim. Acta 1992, 115, 196
  23. Song, X.; Yang, Z.; Xie, Q.; Li, J. J. Organomet. Chem. 1998, 103, 566
  24. Gielen, M.; Biesemans, M.; Vos, D. de; Willem, R. J. Inorg. Biochem. 2000, 79, 139 https://doi.org/10.1016/S0162-0134(99)00161-0
  25. Camacho-Camacho, C.; Vos, D. de; Mahieu, B.; Gielen, M.; Kemmer, M.; Biesemans, M.; Willem, R. Main Group Met. Chem. 2000, 23, 433
  26. Nath, M.; Yadav, R.; Gielen, M.; Dalil, H.; Vos, D. de; Eng, G. Appl. Organomet. Chem. 1997, 11, 727 https://doi.org/10.1002/(SICI)1099-0739(199709)11:9<727::AID-AOC639>3.0.CO;2-X
  27. Kemmer, M.; Biesemans, M.; Willem, R. Main Group Met. Chem. 2000, 23, 433
  28. Masood, M. T.; Ali, S.; Danish, M.; Mazhar, M. Synth. React. Inorg. Met.-Org. Chem. 2002, 32(1), 9 https://doi.org/10.1081/SIM-120013143
  29. Ahmed, S.; Ali, S.; Ahmed, F.; Bhatti, M. H.; Badshah, A.; Mazhar, M.; Khan, K. M. Synth. React. Inorg. Met.-Org. Chem. 2002, 32(8), 1725
  30. Marchetti, F.; Pellei, M.; Pettinari, C.; Pettinari, R.; Rivarola, E.; Santini, C.; Skeltom, B. W.; White, A. H. J. Appl. Organomet. Chem. 2005, 690, 1878 https://doi.org/10.1016/j.jorganchem.2005.01.067
  31. Ali, S.; Khokhar, M. N.; Bhatti, M. H.; Mazhar, M.; Masood, M. T.; Shahid, K.; Badshah, A. Synth. React. Inorg. Met.-Org. Chem. 2002, 32(8), 1579
  32. Ahmad, F.; Ali, S.; Parvez, M.; Munir, A.; Mazhar, M.; Khan, K. M.; Shah, T. A. Heteroatom Chem. 2002, 13(7), 638 https://doi.org/10.1002/hc.10057
  33. Armergo, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 5th ed.; Elsevier: USA, 2003
  34. Deacon, G. B.; Philips, R. J. Coord. Chem. Rev. 1980, 33, 227 https://doi.org/10.1016/S0010-8545(00)80455-5
  35. Ford, B. F. E.; Liengme, B. V.; Sams, J. R. J. Organomet. Chem. 1969, 19, 53 https://doi.org/10.1016/S0022-328X(00)87753-0
  36. Xie, Q.; Yang, Z. Q.; Zhang, Z. X.; Zhang, D. K. Appl. Organomet. Chem. 1992, 6, 193 https://doi.org/10.1002/aoc.590060213
  37. Kalinowski, H. O.; Berger, S.; Brown, S. $^{13}C$ NMR Spectroskopic; Thieme Verlag: Stuttgart, Germany, 1984
  38. Danish, M.; Ali, S.; Mazhar, M.; Badshah, A.; Tieknik, E. R. T. Main Group Met. Chem. 1995, 18, 697
  39. Parvez, M.; Ali, S.; Masood, T. M.; Mazhar, M.; Danish, M. Acta Cryst. 1997, C53, 1211
  40. Meyer, B. N.; Ferrigni, N. R.; Pntnam, J. E.; Jacobson, L. B.; Nicholas, D. E.; McLaughlin, J. L.; Brine Shrimp, J. L. Planta Medica 1982, 45, 31 https://doi.org/10.1055/s-2007-971236
  41. Krigman, M. R.; Silverman, A. P. Neurotoxicology 1984, 5, 129
  42. Barnes, J. M.; Stoner, H. B. Brit. J. Ind. Med. 1958, 15, 15
  43. Kazmi, S. U.; Ali, S. N.; Jamal, S. A.; Rehman, A. J. Phar. Sci. 1991, 4, 113
  44. Blank, H.; Rewbell, G. Arch Derm. 1965, 92, 319 https://doi.org/10.1001/archderm.1965.01600150109021
  45. Shaukat, S. S.; Khan, N. A.; Ahmed, F. Pak. J. Bot. 1980, 12, 97
  46. Molloy, K. C. In The Chemistry of Metal-Carbon Bond; Hrtly, F. R. Ed.; Wiley: New York, 1989

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