Characterization and antimicrobial activity of organotin (IV) complexes of 2-(2',6'-diethylphenylamido) benzoates and 3-(2',6'-diethylphenylamido) propanoates

New organotin(IV) complexes with 2-[(2',6'-diethylphenylamido)]benzoic acid $(HL^1)$ and 3-[(2',6'- diethylphenylamido)]propanoic acid $(HL^2)$ were synthesized by the reaction of di- and triorganotin salts in the presence of triethylamine as base or dioctyltin oxide using a Dean and Stark trap for the removal of azeotropic water. All complexes were characterized by elemental analysis, IR, NMR, and mass spectral studies, and proof that tin-ligand coordination involves only the carboxylate group and complexes show hexa-coordinated geometry in solid state. Multinuclear NMR data show that triorganotin complexes exhibit 4-coordinated geometry while diorganotin complexes show a coordination number greater than 4, probably 5 or 6 in solution state. These complexes were screened to check their antimicrobial activity in vitro. The complexes of 2-[(2',6'-diethylphenylamido)]benzoic acid $(HL^1)$ were also checked for their insecticidal and anti-leishmanial activity. All the complexes show significant activity with few exceptions.

PDF

___

1.B.J. Hollyday and C.A. Mirkin, Main Group Met. Chem. 23, 1 (2000).
2.H. Jiang, Y. Xu, S. Liao, D. Yu, H. Chen and X. Li, J. Mol. Catal. A. 142, 147 (1999).
3.A.K. Sexena, Appl. Organomet. Chem. 16, 1 (1985).
4.A.K. Sexena and F. Huber, Coord. Chem. Rev. 95, 109 (1989).
5.A.C. Belfroid, M. Purperhart and F. Ariese, Mar. Pollu. Bull. 40, 226 (2000).
6.M.M. Whalen, B.F. Longanathan and K. Kannan, Environ Res. 81, 108 (1999).
7.M. Gielen, Appl. Organomet. Chem. 16, 483 (2002).
8.K.C. Molloy, T.G. Purcell, E. Hahn, H. Schumann and J.J. Zukerman, Organometallics. 5, 85 (1986).
9.R.R. Holmes, Ace. Chem. Res. 22, 190 (1989).
10.J.A. Zubita and J.J. Zukerman, Inorg. Chem. 24, 251 (1987).
11.R. Barbieri, A. Silvestri, M. Lo Giudice, G. Ruisi and M.T. Musmeci, J. Chem. Soc. Dalton Trans.519 (1989).
12.S. Shahzadi, S. Ali, M.H. Bhatti, M. Fettouhi and M. Athar, J. Organomet. Chem. 691, 1797 (2006).
13.S. Ali, S.U. Ahmad, S. Shahzadi, Sadiq-ur-Rehman, M. Parvez and M. Mazhar, Appl. Organomet. Chem. 19, 201 (2005).
14.Sadiq-ur-Rehman, S. Ali, M. Mazhar, A. Badshah and M. Parvez, Heteroatom Chem. 17, 420 (2006).
15.S. Shahzadi, K. Shahid, S. AH, M. Mazhar and K.M. Khan, J. Iran. Chem. Soc. 2, 277 (2005).
16.K. Shahid, S. Ali, S. Shahzadi, A. Badshah, K.M. Khan and G.M. Maharvi, Synth. React. Inorg. Met-Org.Chem. 33, 1221 (2003).
17.K. Shahid, S. Shahzadi, S. Ali and M. Mazhar, Bull. Korean Chem. Soc. 27, 44 (2006).
18.S. Shahzadi, K. Shahid, S. Ali, A. Malik, E. Ahmed, U. Rafique, E. Wahab and S. Nawaz, J. Chem. Soc. Pak. 27, 555 (2005).
19.S. Shahzadi, K. Shahid, S. Ali, A. Malik and E. Ahmed, J. Chem. Soc. Pak. 27, 541 (2005).
20.W.L.F. Armarego and-C.L.L. Chai, "Purification of Laboratory Chemicals", 5th ed., Butterworth- Heinemann, London (2003).
21.L.Q. Xie, Z.Q. Yang, Z.X. Zhang and D.K. Zhang, Appl. Organomet. Chem. 6, 193 (1992).
22.Q. Xie, Z. Yang and L. Jiang, Main Group Met. Chem. 19, 509 (1996).
23.H.D. Yin, C.H. Wang, Y. Wang, C.L. Ma, J.X. Shao and J.H. Zhang, Acta Chim. Sinica. 60, 143 (2002).
24.H.D. Yin, C.L. Ma, Y. Wang, H.X. Fang and J.X. Sao, Acta Chim. Sinica. 60, 897 (2002).
25.M. Gielen, E. Joosen, T. Mantilla, K. Jurkschat, R. Willem, C. Roobol, J. Bernheim, G. Atassi, F. Huber, E. Hoffmann, H. Preut and B. Mahieu, Main Group Met. Chem. 18, 27 (1995).
26.S. Shahzadi, K. Shahid, S. Ali, M. Mazhar, A. Badshah, E. Ahmed and A. Malik, Turk. J. Chem. 29, 273 (2005).
27.H.O. Kalinowski, S. Berger and S. Brown, "$^{13}C$ NMR Spectroskopie", Thieme, Stuttgart, Germany (1984).
28.M.H. Bhatti, S. Ali, H. Masood, M. Mazhar and S.I. Qureshi, Synth. React. Inorg. Met-Org. Chem. 30, 1715 (2000).
29.S. Ali, F. Ahmad, M. Mazhar, A. Munir and M.T. Masood, Synth. React. Inorg. Met-Org. Chem. 32, 357 (2001).
30.R. Twari, G. Srivastava, R.C. Mehrotra and A.J. Growe, Inorg. Chim. Acta. 111, 167 (1986).
31.A. Sexena and J.P. Tandon, Polyhedron. 3, 681 (1984).
32.J. Holeeek and A. Lycka, Inorg. Chim. Acta. 118, L15 (1986).
33.F. Ahmad, S. Ali, M. Parvez, A. Munir, M. Mazhar, K.M. Khan and T.A. Shah, Heteroatom Chem. 13, 638 (2002).
34.M. Danish, S. Ali, A. Badshah, M. Mazhar, H. Masood, A. Malik and G. Kehr, Synth. React. Inorg. Met-Org. Chem. 27, 863 (1997).
35.B. Wrackmeyer and G. Kehr, Sü$beta$, J. Chem. Ber. 126, 2221 (1993).
36.A.G. Davis and P.J. Smith, In Comprehensive Organometallic Chemistry; G. Wilkinson, F.G.A. Stone and E.W. Abel, (Eds.); Pergamon Press: Oxford, 2, 519 (1982).
37.B.S. Saraswati and J. Mason, Polyhedron, 5, 1449 (1986).
38.B.N. Meyer, N.R. Ferrigni, J.E. Putnam, L.B. Jacobson, D.E. Nichols and J.L. McLaughlin, Planta Med. 45, 31 (1982).
39.A. Rahman, M.I. Choudhary and W.J. Thomsen, Bioassay Techniques for Drug Development, Harwood Academic Press, Amsterdam (2001).
40.M. Jain, S. Gaur, V.P. Singh and R.V. Singh, Appl. Organomet. Chem. 18, 73 (2004).
41.C. Sexena and R.V. Singh, Phosphorus. Sulfur. Silicon. 97, 17 (1994).
42.R.D. Pearson, A.A. Manian, D. Hall and J.L. Harcus, Antimicrobial Agents and Chemotherapy, 25, 571 (1984).