Browse > Article
http://dx.doi.org/10.5012/bkcs.2006.27.1.044

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)
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.1, 2006 , pp. 44-52 More about this Journal
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
Organotin(IV) carboxylates; Spectroscopic characterization; Biological activity;
Citations & Related Records

Times Cited By Web Of Science : 11  (Related Records In Web of Science)
Times Cited By SCOPUS : 14
연도 인용수 순위
1 Gielen, M.; Lelieveled, P.; Vos, D. de; Pan, H.; Willem, R.; Biesemans, M.; Fiebig, H. H. Inorg. Chim. Acta 1992, 115, 196
2 Tin-Based Antitumor Drugs; NATO ASI Series, H37: Gielen, M., Ed.; Springer-Verlag: Berlin, 1990
3 Krigman, M. R.; Silverman, A. P. Neurotoxicology 1984, 5, 129
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 Gupta, S. P. Chem. Rev. 1994, 94, 1507   DOI   ScienceOn
8 Gielen, M. Coord. Chem. Rev. 1996, 151, 41   DOI   ScienceOn
9 Holloway, C. E.; Melnik, M. Main Group Met. Chem 2000, 23, 555
10 Vasta, C.; Jain, V. K.; Das, T. K.; Tieknik, E. R. T. J. Organomet. Chem. 1991, 21, 421
11 Teoh, S. G.; Ang, S. H.; Looi, E. S.; Keok, C. A.; Teo, S. B.; Fun, H. K. J. Organomet. Chem. 1997, 527, 15   DOI   ScienceOn
12 Sexana, A. K.; Huber, F. Coord. Chem. Rev. 1989, 95, 109   DOI   ScienceOn
13 Barbieri, R. Inorg. Chim. Acta 1992, 191, 253   DOI   ScienceOn
14 Gielen, M.; Biesemans, M.; Vos, D. de; Willem, R. J. Inorg. Biochem. 2000, 79, 139   DOI   ScienceOn
15 Camacho-Camacho, C.; Vos, D. de; Mahieu, B.; Gielen, M.; Kemmer, M.; Biesemans, M.; Willem, R. Main Group Met. Chem. 2000, 23, 433
16 Nath, M.; Yadav, R.; Gielen, M.; Dalil, H.; Vos, D. de; Eng, G. Appl. Organomet. Chem. 1997, 11, 727   DOI   ScienceOn
17 Kemmer, M.; Biesemans, M.; Willem, R. Main Group Met. Chem. 2000, 23, 433
18 Gabbianelli, R.; Villarini, M.; Falcioni, G.; Lupidi, G. Appl. Organomet. Chem. 2002, 16, 163   DOI   ScienceOn
19 Gielen, M.; El-Khloufi, A.; Biesemans, M.; Willem, R.; Meunier- Piert, J. Polyhedron 1992, 11, 1861   DOI   ScienceOn
20 Deacon, G. B.; Philips, R. J. Coord. Chem. Rev. 1980, 33, 227   DOI   ScienceOn
21 Ford, B. F. E.; Liengme, B. V.; Sams, J. R. J. Organomet. Chem. 1969, 19, 53   DOI   ScienceOn
22 Xie, Q.; Yang, Z. Q.; Zhang, Z. X.; Zhang, D. K. Appl. Organomet. Chem. 1992, 6, 193   DOI
23 Armergo, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 5th ed.; Elsevier: USA, 2003
24 Kalinowski, H. O.; Berger, S.; Brown, S. $^{13}C$ NMR Spectroskopic; Thieme Verlag: Stuttgart, Germany, 1984
25 Danish, M.; Ali, S.; Mazhar, M.; Badshah, A.; Tieknik, E. R. T. Main Group Met. Chem. 1995, 18, 697
26 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
27 Tiano, L.; Fedeli, D.; Moretti, M.; Falcioni, G. Appl. Organomet. Chem. 2001, 15, 575   DOI   ScienceOn
28 Ahmad, F.; Ali, S.; Parvez, M.; Munir, A.; Mazhar, M.; Khan, K. M.; Shah, T. A. Heteroatom Chem. 2002, 13(7), 638   DOI   ScienceOn
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 Okawa, R.; Webster, D. E.; Rockow, E. R. J. Am. Chem. Soc. 1960, 82, 3287   DOI
31 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   DOI   ScienceOn
32 Shaukat, S. S.; Khan, N. A.; Ahmed, F. Pak. J. Bot. 1980, 12, 97
33 Molloy, K. C. In The Chemistry of Metal-Carbon Bond; Hrtly, F. R. Ed.; Wiley: New York, 1989
34 Parvez, M.; Ali, S.; Masood, T. M.; Mazhar, M.; Danish, M. Acta Cryst. 1997, C53, 1211
35 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   DOI   ScienceOn
36 Song, X.; Yang, Z.; Xie, Q.; Li, J. J. Organomet. Chem. 1998, 103, 566
37 Vos, D. de; Willem, R.; Gielen, M.; Van Wingerden, K. C.; Nooter, K. Met. Based Drugs 1998, 5, 179   DOI   ScienceOn
38 Tieknik, E. R. T. Appl. Organomet. Chem. 1991, 5, 1   DOI
39 Barnes, J. M.; Stoner, H. B. Brit. J. Ind. Med. 1958, 15, 15
40 Masood, M. T.; Ali, S.; Danish, M.; Mazhar, M. Synth. React. Inorg. Met.-Org. Chem. 2002, 32(1), 9   DOI   ScienceOn
41 Ng, S. W.; Kumar Das, V. G.; Tieknik, E. R. T. J. Organomet. Chem. 1991, 111, 403
42 Molloy, K. C.; Purcell, T. G.; Schumann, H.; Zuckerman, J. J. Organometallics 1986, 5, 85   DOI
43 Blank, H.; Rewbell, G. Arch Derm. 1965, 92, 319   DOI
44 Kazmi, S. U.; Ali, S. N.; Jamal, S. A.; Rehman, A. J. Phar. Sci. 1991, 4, 113
45 Honnik, W. D.; Zuckerman, J. J. J. Organomet. Chem. 1979, 133, 178
46 Harrison, P. G.; Philips, R. C. J. Organomet. Chem. 1979, 37, 182