Synthesis, crystal structure and biological activity of bis(acetone thiosemicarbazone-S)dichlorodiphenyltin(IV)

Abstract

The reaction between diphenyltin(IV) dichloride and thiosemicarbazide using acetone–ethanol as solvent resulted in the formation of bis(acetone thiosemicarbazone-S)dichlorodiphenyltin(IV), SnPh₂Cl₂(atsc)₂. The crystal structure determination of the compound revealed it to be a monomeric six-co-ordinated organotin(IV) complex. Each of the two atsc functions as a monodentate ligand, co-ordinating to the tin atom through the sulfur atom and conferring a distorted-octahedral geometry upon the tin. The Sn–S bond length is 2.712(1) Å. The antifungal activity of the complex, atsc and SnPh₂Cl₂ against four plant pathogens has been evaluated. The complex displays marked fungitoxicity against these fungi and is more fungitoxic than free atsc and SnPh₂Cl₂. It has also shown significant cytotoxicity against human colon adenocarcinoma, breast adenocarcinoma, hepatocellular carcinoma and acute lymphoblastic leukaemia.

References

1. J. Valdes-Martinez, A. Sierra-Romero, C. Alvarez-Toledano, R. A. Toscano and H. Garcia-Tapia, J. Organomet. Chem., 1983, 352, 321.
2. Kiran, R. V. Singh and J. P. Tandon, Synth. React. Inorg. Metal-Org. Chem., 1986, 16, 1341.
3. M. Nath, N. Sharma and C. L. Sharma, Synth. React. Inorg. Metal-Org. Chem., 1989, 19, 339.
4. V. K. Arora, K. B. Pandeya and R. P. Singh, J. Indian Chem. Soc., 1979, 56, 656.
5. P. L. Maurya, B. V. Agarwala and A. K. Dey, J. Indian Chem. Soc., 1980, 57, 275.
6. A. K. Saxena, J. K. Koacher and J. P. Tandon, J. Inorg. Nucl. Chem., 1981, 43, 3091.
7. A. Saxena and J. P. Tandon, Polyhedron, 1984, 3, 681.
8. A. Varshney and J. P. Tandon, Polyhedron, 1986, 5, 739.
9. G. M. Sheldrick, SHELXTL PC^™, Release 4.1, Siemens Crystallographic Research Systems, Madison, WI, 1990.
10. M. J. M. Campbell, Coord. Chem. Rev., 1975, 15, 279.
11. S. Padhye and G. B. Kauffman, Coord. Chem. Rev., 1985, 63, 127.
12. G. J. Palenik, Acta Crystallogr., Sect. B, 1974, 30, 2390.
13. J. Valdes-Martinez, R. A. Toscano, M. Soriano-Garcia, M. Rubio, J. Gomez-Lara, M. A. Vazquez-M and S. Carranza, Polyhedron, 1989, 8, 727.
14. R. Restivo and G. J. Palenik, Acta Crystallogr., Sect. B, 1970, 26, 1397.
15. M. K. Kokila, Puttaraja, M. V. Kulkarni and S. Thampi, Acta Crystallogr., Sect. C, 1995, 51, 330.
16. M. Mathew and G. J. Palenik, J. Am. Chem. Soc., 1969, 91, 6310.
17. S. W. Ng, V. G. Kumar Das, B. W. Skelton and A. H. White, J. Organomet. Chem., 1989, 377, 211.
18. C. Bellito, D. Gattegno, A. M. Giuliani and M. Bossa, J. Chem. Soc., Dalton Trans., 1976, 758.
19. P. Umpathy, A. P. Budhkar and C. S. Dorai, J. Indian Chem. Soc., 1986, 63, 714.
20. T. T. Bamgboye and O. A. Bamgboye, Inorg. Chim. Acta, 1987, 133, 247.
21. K. N. Thimmaiah, G. T. Chandrappa, Rangaswamy and Jayarama, Polyhedron, 1984, 3, 1237.
22. A. Albert and R. J. Goldere, Nature (London), 1948, 161, 95.